JPH0449274A - Novel tetraselenotetracene and complex containing the same - Google Patents
Novel tetraselenotetracene and complex containing the sameInfo
- Publication number
- JPH0449274A JPH0449274A JP15844390A JP15844390A JPH0449274A JP H0449274 A JPH0449274 A JP H0449274A JP 15844390 A JP15844390 A JP 15844390A JP 15844390 A JP15844390 A JP 15844390A JP H0449274 A JPH0449274 A JP H0449274A
- Authority
- JP
- Japan
- Prior art keywords
- compound
- formula
- charge transfer
- transfer complex
- electron
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- GHIAGEOCQFIEQP-UHFFFAOYSA-N C1[Se][Se]C=C1 Chemical compound C1[Se][Se]C=C1 GHIAGEOCQFIEQP-UHFFFAOYSA-N 0.000 claims abstract description 5
- XXDLUMFPBQPJCM-UHFFFAOYSA-N 1,4,5,12-tetrachlorotetracene Chemical compound C1=CC=C2C=C(C(Cl)=C3C(Cl)=CC=C(Cl)C3=C3Cl)C3=CC2=C1 XXDLUMFPBQPJCM-UHFFFAOYSA-N 0.000 claims abstract 2
- 239000000370 acceptor Substances 0.000 claims description 17
- 239000000126 substance Substances 0.000 claims description 5
- HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 claims description 3
- DFJXWQJAMNCPII-UHFFFAOYSA-N 2-[4-(dicyanomethylidene)-2,5-dimethylcyclohexa-2,5-dien-1-ylidene]propanedinitrile Chemical compound CC1=CC(=C(C#N)C#N)C(C)=CC1=C(C#N)C#N DFJXWQJAMNCPII-UHFFFAOYSA-N 0.000 claims description 3
- PCCVSPMFGIFTHU-UHFFFAOYSA-N tetracyanoquinodimethane Chemical group N#CC(C#N)=C1C=CC(=C(C#N)C#N)C=C1 PCCVSPMFGIFTHU-UHFFFAOYSA-N 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 2
- UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 claims description 2
- NLDYACGHTUPAQU-UHFFFAOYSA-N tetracyanoethylene Chemical group N#CC(C#N)=C(C#N)C#N NLDYACGHTUPAQU-UHFFFAOYSA-N 0.000 claims description 2
- WRTMQOHKMFDUKX-UHFFFAOYSA-N triiodide Chemical compound I[I-]I WRTMQOHKMFDUKX-UHFFFAOYSA-N 0.000 claims description 2
- IXHWGNYCZPISET-UHFFFAOYSA-N 2-[4-(dicyanomethylidene)-2,3,5,6-tetrafluorocyclohexa-2,5-dien-1-ylidene]propanedinitrile Chemical compound FC1=C(F)C(=C(C#N)C#N)C(F)=C(F)C1=C(C#N)C#N IXHWGNYCZPISET-UHFFFAOYSA-N 0.000 claims 1
- DNXUGBMARDFRGG-UHFFFAOYSA-N 3,6-dioxocyclohexa-1,4-diene-1,2-dicarbonitrile Chemical compound O=C1C=CC(=O)C(C#N)=C1C#N DNXUGBMARDFRGG-UHFFFAOYSA-N 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- -1 bromoanil Chemical compound 0.000 claims 1
- XKHYPFFZHSGMBE-UHFFFAOYSA-N buta-1,3-diene-1,1,2,3,4,4-hexacarbonitrile Chemical compound N#CC(C#N)=C(C#N)C(C#N)=C(C#N)C#N XKHYPFFZHSGMBE-UHFFFAOYSA-N 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 125000003963 dichloro group Chemical group Cl* 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 46
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract description 8
- 239000002904 solvent Substances 0.000 abstract description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract description 6
- 239000003960 organic solvent Substances 0.000 abstract description 6
- 229910052711 selenium Inorganic materials 0.000 abstract description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 5
- 229910052708 sodium Inorganic materials 0.000 abstract description 4
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 abstract description 3
- RPSIZDRFWOFFIH-UHFFFAOYSA-N 1,4,5,5,12,12-hexachlorotetracene Chemical compound C1=CC=C2C=C(C(C=3C(Cl)=CC=C(C=3C3(Cl)Cl)Cl)(Cl)Cl)C3=CC2=C1 RPSIZDRFWOFFIH-UHFFFAOYSA-N 0.000 abstract description 2
- KXSCLYAOGKUTBX-UHFFFAOYSA-N 5,12-dihydroxy-2,3-dihydrotetracene-1,4-dione Chemical compound C1=CC=C2C=C3C(O)=C(C(=O)CCC4=O)C4=C(O)C3=CC2=C1 KXSCLYAOGKUTBX-UHFFFAOYSA-N 0.000 abstract description 2
- 229910021626 Tin(II) chloride Inorganic materials 0.000 abstract description 2
- 229910000288 alkali metal carbonate Inorganic materials 0.000 abstract description 2
- 150000008041 alkali metal carbonates Chemical class 0.000 abstract description 2
- 235000011150 stannous chloride Nutrition 0.000 abstract description 2
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 abstract description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 abstract 2
- UJBYMXXGKDMLGF-UHFFFAOYSA-N 1,4-dihydroxytetracene-5,12-dione Chemical compound C1=CC=C2C=C(C(=O)C=3C(O)=CC=C(O)C=3C3=O)C3=CC2=C1 UJBYMXXGKDMLGF-UHFFFAOYSA-N 0.000 abstract 1
- GRWZHXKQBITJKP-UHFFFAOYSA-L dithionite(2-) Chemical compound [O-]S(=O)S([O-])=O GRWZHXKQBITJKP-UHFFFAOYSA-L 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 description 10
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 239000002244 precipitate Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 5
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 5
- 230000000704 physical effect Effects 0.000 description 5
- 230000035484 reaction time Effects 0.000 description 5
- 239000011669 selenium Substances 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- FHCPAXDKURNIOZ-UHFFFAOYSA-N tetrathiafulvalene Chemical compound S1C=CSC1=C1SC=CS1 FHCPAXDKURNIOZ-UHFFFAOYSA-N 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 4
- 238000000921 elemental analysis Methods 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- DIKBFYAXUHHXCS-UHFFFAOYSA-N bromoform Chemical compound BrC(Br)Br DIKBFYAXUHHXCS-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000002484 cyclic voltammetry Methods 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
- UBOXGVDOUJQMTN-UHFFFAOYSA-N 1,1,2-trichloroethane Chemical compound ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- SZPDSSCEOCVFMN-UHFFFAOYSA-N 1,2,3,4-tetrachlorotetracene Chemical compound C1=CC=CC2=CC3=CC4=C(Cl)C(Cl)=C(Cl)C(Cl)=C4C=C3C=C21 SZPDSSCEOCVFMN-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- JTPNRXUCIXHOKM-UHFFFAOYSA-N 1-chloronaphthalene Chemical compound C1=CC=C2C(Cl)=CC=CC2=C1 JTPNRXUCIXHOKM-UHFFFAOYSA-N 0.000 description 1
- JLTPSDHKZGWXTD-UHFFFAOYSA-N 2-[6-(dicyanomethylidene)naphthalen-2-ylidene]propanedinitrile Chemical compound N#CC(C#N)=C1C=CC2=CC(=C(C#N)C#N)C=CC2=C1 JLTPSDHKZGWXTD-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical group C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- 102100025683 Alkaline phosphatase, tissue-nonspecific isozyme Human genes 0.000 description 1
- 101710161969 Alkaline phosphatase, tissue-nonspecific isozyme Proteins 0.000 description 1
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 238000000944 Soxhlet extraction Methods 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 229950005228 bromoform Drugs 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- QGJOPFRUJISHPQ-NJFSPNSNSA-N carbon disulfide-14c Chemical compound S=[14C]=S QGJOPFRUJISHPQ-NJFSPNSNSA-N 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- LWJYMKDMGMOTSB-UHFFFAOYSA-L dichlorotin;hydrate Chemical compound O.Cl[Sn]Cl LWJYMKDMGMOTSB-UHFFFAOYSA-L 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000007769 metal material Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 125000003748 selenium group Chemical group *[Se]* 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000003115 supporting electrolyte Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- LZPBKINTWROMEA-UHFFFAOYSA-N tetracene-5,12-dione Chemical compound C1=CC=C2C=C3C(=O)C4=CC=CC=C4C(=O)C3=CC2=C1 LZPBKINTWROMEA-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
【発明の詳細な説明】
（産業上の利用分野）
本発明は高導電性の電荷移動錯体及びその成分である電
子供与体に関する。DETAILED DESCRIPTION OF THE INVENTION (Industrial Application Field) The present invention relates to a highly conductive charge transfer complex and an electron donor which is a component thereof.
（従来技術と発明が解決しようとする課！り有機高導電
性物質は銅やアルミニウム等の金属材料に比べ軽量であ
り腐蝕性がないこと等から近年特に注目されつつある。(Issues to be solved by the prior art and the invention!) Organic highly conductive materials have been attracting particular attention in recent years because they are lighter and less corrosive than metal materials such as copper and aluminum.
一般に有機物質は電気絶縁性であるが、これに導電性を
付与するには電荷移動錯体を形成させるのがよく、これ
までに種々の電子供与体と電子受容体が合成され、これ
らの組合せから多数の導電性電荷移動錯体が提出されて
いる。Generally, organic substances are electrically insulating, but in order to impart electrical conductivity to them, it is best to form a charge transfer complex.To date, various electron donors and electron acceptors have been synthesized, and various combinations of electron donors and electron acceptors have been synthesized. A large number of conductive charge transfer complexes have been proposed.
これらの中で電子供与体成分としてはテトラチアフルバ
レン（ＴＴＦ）、テトラセレノテトラセン（ＴＳｅＴ）
等が効果的な電子供与体としてしばしば利用されている
。Among these, tetrathiafulvalene (TTF) and tetraselenotetracene (TSeT) are used as electron donor components.
etc. are often used as effective electron donors.
しかしＴＳｅＴはその錯体の導電性の点で末だ充分とは
言えないだけでなく、溶解性の点でも問題があり、錯体
を合成する際に溶剤の選択、濃度等で一定の制約を受け
ていた。However, TSeT not only has insufficient conductivity as a complex, but also has problems in solubility, and there are certain restrictions on the selection of solvent, concentration, etc. when synthesizing the complex. Ta.
（課題を解決するための手段）
本発明者らは、上記の点に鑑み、導電性に優れた電荷移
動錯体を与え、しかも優れた溶解性を有する電子供与性
を得る目的で鋭意検討した。その結果、ＴＳｅＴのセレ
ンの結合位置を変え、非対称の電子供与体とすることに
より、ＴＴＦより溶解性が改善されるだけでなく、これ
と他成分の電子受容体で形成される電荷移動錯体が高導
電性を有することを見出し本発明を完成させるに至った
ものである。(Means for Solving the Problems) In view of the above points, the present inventors conducted extensive studies with the aim of providing a charge transfer complex with excellent conductivity and electron donating properties with excellent solubility. As a result, by changing the bonding position of selenium in TSeT and making it an asymmetric electron donor, not only the solubility is improved compared to TTF, but also the charge transfer complex formed with this and other electron acceptors is It was discovered that it has high conductivity, and the present invention was completed.
すなわち本発明は下記式（Ｉ）で表わされるナフタセン
［１，１２−ｃｄ ： ４，５−’ｃ’ ｄ’コビス
［１，２］ジセレノール及び化合物（Ｉ）と他成分の電
子受容体で形成された電荷移動錯体、更に化合物（１）
の合成中間体である下記式（Ｉｔ）で表わされる１、４
，５．１２−テトラクロロナフタセン。That is, the present invention relates to naphthacene [1,12-cd: 4,5-'c'd' cobis[1,2] diselenol represented by the following formula (I), compound (I), and an electron acceptor of other components. charge transfer complex, and further compound (1)
1,4 represented by the following formula (It), which is a synthetic intermediate of
, 5.12-tetrachloronaphthacene.
下記式（Ｉ［Ｉ）で表わされる１、４，５，５．１２．
１２−へキサクロロ−５，１２−ジヒドロナフタセン及
び下記式（ＩＶ）で表わされる２、３−ジヒドロ−５，
１２−ジヒドロキシ−１，４
するものである。1, 4, 5, 5.12. represented by the following formula (I[I).
12-hexachloro-5,12-dihydronaphthacene and 2,3-dihydro-5, represented by the following formula (IV),
12-dihydroxy-1,4.
ナフタセンキノンを提供
本発明の化合物（１）〜（■）は下記のようにして公知
の反応によって合成することができる。Compounds (1) to (■) of the present invention that provide naphthacenequinone can be synthesized by known reactions as described below.
ＯＨ
＝ （■）→ （Ｉ）
ａ）化合物（ＩＶ）の合成
１．４−ジヒドロキシ−５，１２−ナフタセンキノン（
イ）を水溶性有機溶媒中、水の存在下アルカリ金属炭酸
塩とナトリウム又はカリウムハイドロサルファイドで処
理することによって、２，３−ジヒドロ−５，１２−ジ
ヒドロキシ−１，４−ナフタセンキノン（化合物（■）
）が得られる。OH = (■)→ (I) a) Synthesis of compound (IV) 1.4-dihydroxy-5,12-naphthacenequinone (
2,3-dihydro-5,12-dihydroxy-1,4-naphthacenequinone (compound (■ )
) is obtained.
水溶性有機溶媒としてはアセトン、Ｎ−Ｎ−ジメチルホ
ルムアルデヒド、ジメチルスルホキシド等が挙げられる
。アルカリ金属炭酸塩としては炭酸ナトリウム、炭酸カ
リウム等が挙げられる０反応部度は０〜１００℃、反応
時間は０．５〜１０時間の範囲が適当であ２．。Examples of water-soluble organic solvents include acetone, N-N-dimethyl formaldehyde, dimethyl sulfoxide, and the like. Examples of the alkali metal carbonates include sodium carbonate, potassium carbonate, etc. The reaction temperature is preferably 0 to 100°C, and the reaction time is suitably in the range of 0.5 to 10 hours. .
ｂ）化合物（ＩＩＩ）の合成
化合物（ＩＶ）を有機溶媒中五塩化リンで処理すること
によって、１，４，５，５，１２．１２−ヘキサクロロ
−５，１２−ジヒドロナフタセン（化合物（■））が得
られる。有機溶媒としては、ベンゼン、トルエン、キシ
レン、クロロベンゼン、ジクロロベンゼン、１−クロロ
ナフタレン等が挙げられる。反応温度は５０〜１６０℃
、反応時間は０．５〜５０時間の範囲が適当である。b) Synthesis of compound (III) By treating compound (IV) with phosphorus pentachloride in an organic solvent, 1,4,5,5,12.12-hexachloro-5,12-dihydronaphthacene (compound (■ )) is obtained. Examples of the organic solvent include benzene, toluene, xylene, chlorobenzene, dichlorobenzene, 1-chloronaphthalene, and the like. Reaction temperature is 50-160℃
The reaction time is suitably in the range of 0.5 to 50 hours.
Ｃ）化合物（Ｉｆ）の合成
化合物（ＩＩＩ）を酢酸溶媒中濃塩酸の存在下二塩化ス
ズで処理すると、１．４．５．１２〒テトラクロロナフ
タセン（化合物（■））が得られる０反応部度は８０〜
１６０℃、反応時間は０．５〜１０時間が適当である。C) Synthesis of compound (If) Compound (III) is treated with tin dichloride in the presence of concentrated hydrochloric acid in an acetic acid solvent to obtain 1.4.5.12 tetrachloronaphthacene (compound (■))0 The reaction part degree is 80~
A temperature of 160°C and a reaction time of 0.5 to 10 hours are appropriate.
ｄ）化合物（Ｉ）の合成
化合物（ＩＩ）をＮ、Ｎ−ジメチルホルムアミド中で、
ナトリウム及びセレンで処理するとナフタセン ［１，
１２−ｃ ｄ ： ４，５−ｃ’ ｄ’ ］ ビス［１
゜２コジセレノール（化合物（Ｉ））が得られる０反応
部度は８０〜１６０℃、反応時間は０．５〜５０時間が
適当である。化合物（１）はまた化合物（ＩＩＩ）から
直接合成することもできる。すなわち化合物（ＩＩＩ）
をＮ、Ｎ−ジメチルホルムアミド中でナトリウム及びセ
レンで処理すると化合物（１）が得られる。反応温度は
８０〜１６０℃、反応時間は０．５〜５０時間が適当で
ある。d) Synthesis of compound (I) Compound (II) in N,N-dimethylformamide,
When treated with sodium and selenium, naphthacene [1,
12-c d : 4,5-c'd' ] bis[1
It is appropriate that the degree of reaction at which 2-codiselenol (compound (I)) is obtained is from 80 to 160°C, and the reaction time is from 0.5 to 50 hours. Compound (1) can also be directly synthesized from compound (III). That is, compound (III)
Compound (1) is obtained by treating with sodium and selenium in N,N-dimethylformamide. Suitable reaction temperature is 80 to 160°C and reaction time is 0.5 to 50 hours.
ｅ） ｌｆｔ荷移動錯体の合成
化合物（１）を電子供与体とする電荷移動錯体は、化合
物（Ｉ）及び電子受容体をそれぞれ室温又は加熱下で溶
媒に溶解した溶液を混合するか、又は化合物（１）と電
子受容体を加熱上溶媒に溶解した溶液を冷却することに
よって得られる０組成比は化合物（Ｉ）に対する電子受
容体のモル比で０．２５〜５が適当である。e) Synthesis of lft charge transfer complex A charge transfer complex using compound (1) as an electron donor can be prepared by mixing a solution of compound (I) and an electron acceptor dissolved in a solvent at room temperature or under heating, or by mixing a solution of compound (I) and an electron acceptor dissolved in a solvent at room temperature or under heating, or The 0 composition ratio obtained by heating and cooling a solution of (1) and an electron acceptor dissolved in a solvent is suitably a molar ratio of electron acceptor to compound (I) of 0.25 to 5.
電子受容体としては、７．７．８．８−テトラシアノキ
ノジメタン、 ２，３，５．６−テトラフルオロ−７
．７゜８．８−テトラシアノキノジメタン、２，５−ジ
メチル−７、７，８，８−テトラシアノキノジメタン、
１１゜１１．１２．１２−テトラシアノ−２，６−ナフ
トキノジメタン、２．３−ジクロロ−５，６−ジシアツ
ベンゾキノン、 １．１．２．３．４．４−ヘキサシ
アノブタジェン、テトラシアノエチレン、ジクロロジシ
アノベンソｔ−ノン、クロラニル、ブロモアニル、 塩
８゜臭素、ヨウ素、トリヨーダイド等が挙げられる。As an electron acceptor, 7.7.8.8-tetracyanoquinodimethane, 2,3,5.6-tetrafluoro-7
．． 7゜8.8-tetracyanoquinodimethane, 2,5-dimethyl-7,7,8,8-tetracyanoquinodimethane,
11゜11.12.12-tetracyano-2,6-naphthoquinodimethane, 2.3-dichloro-5,6-dicyazbenzoquinone, 1.1.2.3.4.4-hexacyanobutadiene, tetra Examples include cyanoethylene, dichlorodicyanobenzot-one, chloranil, bromoanil, 8° bromine salt, iodine, triiodide and the like.
有機溶媒としては、ベンゼン、トルエン、キシレン等の
芳香族炭化水素、四塩化炭素、ジクロロメタン、塩化メ
チレン、１．２−ジクロロエタン。Examples of organic solvents include aromatic hydrocarbons such as benzene, toluene, and xylene, carbon tetrachloride, dichloromethane, methylene chloride, and 1,2-dichloroethane.
１．１．２−）ジクロロエタン。１，１．１−トリクロ
ロエタン、ブロモホルム、１．２−ジブロモエタン等の
ハロゲン化炭化水素或いは二硫化炭素等が挙げられる。1.1.2-) Dichloroethane. Examples include halogenated hydrocarbons such as 1,1.1-trichloroethane, bromoform, and 1,2-dibromoethane, and carbon disulfide.
（発明の効果）
＋１１ 本発明のナフタセン［１，１２−ｃｄ ：
４，５Ｃ′ｄ′］ビス［１，２］ジセレノールはＴＴＦ
より優れた電子供与性を有する電子供与体である。(Effect of the invention) +11 Naphthacene [1,12-cd:
4,5C′d′]bis[1,2]diselenol is TTF
It is an electron donor with superior electron donating properties.
（２）本発明の新規電子供与体はＴＳｅＴより優れた溶
解性を有するだけでなく、これと他成分の電子受容体で
形成される電荷移動錯体は高い導電性を有する。(2) Not only does the novel electron donor of the present invention have better solubility than TSeT, but the charge transfer complex formed with it and other electron acceptors has high conductivity.
このように本発明は工業的価値の大きいものということ
ができる。Thus, the present invention can be said to be of great industrial value.
（実施例）
以下本発明を実施例によって具体的に説明するが、本発
明はこれらに限定されるものではない。(Examples) The present invention will be specifically described below with reference to Examples, but the present invention is not limited thereto.
実施例１
化合物（イ）２１ｇ、無水炭酸ナトリウム１７．５ｇ、
アセトン３５０ｍｌ及び水３５０ｍＡの混合物を１時間
撹拌した後、ナトリウムハイドロサルファイ）３５ｇを
加え、室温で１時間、更に還流下１時間反応させる。水
５００ｍｆを加え、生成した沈澱を集めて乾燥する。得
られた沈澱をクロロホルム６００ｍＡ！に溶解し、短い
シリカゲルカラムを通した後沖液を約１００ｍｌにまで
濃縮し、これをヘキサン２００ｍｌで希釈すると黄色針
状結晶として化合物（ＩＶ）が得られる（１７．０ｇ。Example 1 Compound (a) 21g, anhydrous sodium carbonate 17.5g,
After stirring a mixture of 350 ml of acetone and 350 mA of water for 1 hour, 35 g of sodium hydrosulfite was added, and the mixture was reacted for 1 hour at room temperature and then for 1 hour under reflux. Add 500 mf of water, collect and dry the precipitate formed. The obtained precipitate was heated with chloroform at 600 mA! After passing through a short silica gel column, the Oki liquid was concentrated to about 100 ml and diluted with 200 ml of hexane to obtain compound (IV) as yellow needle crystals (17.0 g).
収率８０％）。yield 80%).
化合物（ＩＶ）の物性値
融点 ２３０〜２３２℃
ＩＲ１６２０ｃｍ−’（Ｃ＝Ｏ）
’Ｈ−ＮＭＲ（τ）
３．０６２ （４Ｈ，ｓ、 ＣＨｚ）、 ７．６０
〜７．７０ （２Ｈ，ｍ、芳香族Ｈ）。Physical properties of compound (IV) Melting point 230-232°C IR1620cm-'(C=O)'H-NMR(τ) 3.062 (4H,s, CHz), 7.60
~7.70 (2H,m, aromatic H).
８．０４〜８．１５ （２Ｈ，ｍ、芳香族Ｈ）。8.04-8.15 (2H, m, aromatic H).
８．９６５ （２Ｈ，ｓ、芳香族Ｈ）。8.965 (2H,s, aromatic H).
１４．１２２ （２Ｈ，ｓ、ＯＨ）
元素分析
実測値 Ｃ７３，８９，Ｈ４，００％
Ｃ＋ｓＨ＋ｔＯ４としての計算値
Ｃ７３，９７，Ｈ４，１４％
実施例２
化合物（ＩＶ）１０ｇ、五塩化リン４２．７ ｇ及び０
−クロロベンゼン１６ｍｊ！の混合物を１４０℃で２４
時間反応させる。生じた沈澱を堀遇し、沈澱を石油エー
テルで洗浄すると白色プリズム状の結晶として化合物（
ＩＩＩ）が得られる（７．３７ｇ。14.122 (2H, s, OH) Actual elemental analysis value C73,89, H4,00% Calculated value as C+sH+tO4 C73,97, H4,14% Example 2 Compound (IV) 10g, phosphorus pentachloride 42.7 g and 0
-Chlorobenzene 16mj! of the mixture at 140°C for 24
Allow time to react. When the formed precipitate is excavated and washed with petroleum ether, the compound (
III) is obtained (7.37 g.
収率４９％）。yield 49%).
化合物（ＤＩ）の物性値 融点 １６３℃（分解） ＩＲ１５６０，１５９０ｃｍ−’ ’Ｈ−ＮＭＲ（τ） ６．７５０ （２Ｈ，ｓ、芳香族Ｈ）。Physical property values of compound (DI) Melting point: 163℃ (decomposition) IR1560,1590cm-' 'H-NMR(τ) 6.750 (2H,s, aromatic H).
７．４０〜７．７０ （４Ｈ，ｍ、芳香族Ｈ）。7.40-7.70 (4H, m, aromatic H).
７．６２３ （２Ｈ，ｓ、芳香族Ｈ）
ＭＳ （ｍ／ｚ） ４３６ （Ｍ”）、４０１元素
分析
実測値 Ｃ４９，４４，Ｈｌ、７７％
ＣＩ ＠ Ｈｓ Ｃ１ｂとしての計算値Ｃ４９，４８％
、Ｈｌ、８５％
実施例３
化合物Ｃｍ）１．３１ｇ、二塩化スズ水和物２６．６ｇ
、濃塩酸３２．７ ｍ ｊ！及び酢酸４３．６ ｍ Ｉ
ｔの混合物を２時間撹拌する。水２００ｍｌを加え、生
じた沈澱を集め、これをアルミナカラムクロマトグラフ
ィーでクロロホルムを溶離液として精製した後クロロベ
ンゼンで再結晶すると針状結晶として化合物（ｎ）が得
られる（４．９０ｇ、収率７９％）。7.623 (2H, s, aromatic H) MS (m/z) 436 (M”), 401 elemental analysis actual value C49,44, Hl, 77% CI @ Hs Calculated value as C1b C49,48%
, Hl, 85% Example 3 Compound Cm) 1.31 g, tin dichloride hydrate 26.6 g
, concentrated hydrochloric acid 32.7 m j! and acetic acid 43.6 m I
Stir the mixture for 2 hours. Add 200 ml of water, collect the resulting precipitate, purify it by alumina column chromatography using chloroform as an eluent, and then recrystallize from chlorobenzene to obtain compound (n) as needle-shaped crystals (4.90 g, yield 79 %).
化合物（ＩＩ）の物性値
融点 ２５７〜２５９℃
ＩＲ１５９５，１２９０，８８０ｃｍ−’’Ｈ−ＮＭＲ
（τ）
７．４０８ （２Ｈ，ｓ、芳香族Ｈ）。Physical properties of compound (II) Melting point 257-259°C IR1595, 1290, 880cm-''H-NMR
(τ) 7.408 (2H,s, aromatic H).
７．５０〜７．６１（２Ｈ，芳香族Ｈ）。7.50-7.61 (2H, aromatic H).
８．０７〜８．１８ （２Ｈ，ｍ、芳香族Ｈ）。8.07-8.18 (2H, m, aromatic H).
９．３０７ （２Ｈ，ｓ、芳香族Ｈ）元素分析
実測値 Ｃ５９，０６，Ｈ２，２６％
Ｃｌ＊ Ｈｓ Ｃｊ！ ４としての計算値Ｃ５９，０６
，Ｈ２，２０％
実施例４
Ｎ、Ｎ−ジメチルホルムアミド５０ ｍ ｌ中ナトリウ
ム０．２０２ｇとセレン０．６９５ ｇのサスペンショ
ンを１３０℃で２時間撹拌する。温度を８０℃まで下げ
た後化合物（ｎ）０．７３２ｇを加えその温度で２００
時間反応続ける。室温に冷却した後生じた沈澱を集め、
水及びアセトンで洗浄し０、ｌｍｍＨｇの減圧下１００
℃で乾燥する。9.307 (2H, s, aromatic H) elemental analysis actual value C59,06,H2,26% Cl* Hs Cj! Calculated value as 4 C59,06
, H2, 20% Example 4 A suspension of 0.202 g of sodium and 0.695 g of selenium in 50 ml of N,N-dimethylformamide is stirred at 130 DEG C. for 2 hours. After lowering the temperature to 80°C, 0.732g of compound (n) was added and heated at that temperature for 200°C.
Continue to react for hours. Collect the resulting precipitate after cooling to room temperature,
Washed with water and acetone, 0, 100 under vacuum of lmmHg.
Dry at °C.
この沈澱を二硫化炭素を用いてソックスレー抽出を行な
い、抽出物を集め二硫化炭素で再結晶すると深緑色の結
晶として化合物（１）が得られる（０．３２９ｇ、収率
３０％）。This precipitate was subjected to Soxhlet extraction using carbon disulfide, and the extracts were collected and recrystallized with carbon disulfide to obtain compound (1) as dark green crystals (0.329 g, yield 30%).
化合物（１）の物性値
融点 ３００℃
ＭＳ （ｍ／ｚ） ５４２ （Ｍ”）元素分析
実測値 Ｃ４０，２８，Ｈｌ、４２％
Ｃ＋＋＋ＨｓＳｅ４とシテ（Ｄ計算ｇｌＣ４０，０３，
Ｈｌ、４９％
化合物（１）は塩化メチレン、二硫化炭素の溶媒に対し
、ＴＳｅＴより５倍以上の溶解性を示す。Physical properties of compound (1) Melting point 300°C MS (m/z) 542 (M”) Actual elemental analysis value C40,28, Hl, 42% C+++HsSe4 and shite (D calculation glC40,03,
Hl, 49% Compound (1) exhibits a solubility in methylene chloride and carbon disulfide solvents that is 5 times or more higher than that of TSeT.
実施例５
実施例４と同様にして化合物（ＩＩ［）１．０９ｇをＮ
、Ｎ−ジメチルホルムアミド７５ｍｊ！中ナトジナトリ
ウム０７５ ｇとセレン０．８９６ ｇを用いて８０℃
で２０時間処理すると化合物（Ｉ）が得られる（０．２
７５ｇ、収率２０％）。Example 5 In the same manner as in Example 4, 1.09 g of compound (II[) was added with N
, N-dimethylformamide 75mj! 80℃ using 075 g of sodium chloride and 0.896 g of selenium.
Compound (I) is obtained by treatment for 20 hours (0.2
75g, yield 20%).
実施例６ 参考例
化合物（１）についてサイクリックボルタメトリーを行
ない、半波酸化電位を求めた結果を第１表に示した。Example 6 Reference Example Compound (1) was subjected to cyclic voltammetry to determine the half-wave oxidation potential. The results are shown in Table 1.
サイクリックボルタメトリーは支持電解質として０．Ｉ
Ｍのテトラブチルアンモニウムバークロレートを含むベ
ンゾニトリル溶液で行い、白金作用電極とＡｇ／ＡｇＣ
１参照電極を用いた。スキャン速度は１００ｍＶ／ｓｅ
ｃである。Cyclic voltammetry was carried out using 0.0% as the supporting electrolyte. I
carried out in a benzonitrile solution containing tetrabutylammonium verchlorate of M, with a platinum working electrode and Ag/AgC
1 reference electrode was used. Scan speed is 100mV/se
It is c.
参考例として上記と同様にして’ｒｓｅＴ。As a reference example, 'rseT' in the same manner as above.
ＴＴＦの半波酸化電位を求めた結果を第１表に併せて示
した。The results of determining the half-wave oxidation potential of TTF are also shown in Table 1.
化合物（１）＋ ０．２７ ＋０．６０参考例
ＴＳ ｅＴ ＋０．２１ ＋０．５６実
施例７
化合物（１）と第２表に示した電子受容体を加熱下１，
１．２−トリクロロエタンの飽和溶液とした後冷却して
析出した沈澱を集めて電荷移動錯体を得た。用いた電子
受容体と得られた電荷移動錯体の物性値を第２表に示し
た。表中電子受容体の略号の意味は次のとおりである。Compound (1) + 0.27 +0.60 Reference Example TS eT +0.21 +0.56 Example 7 Compound (1) and the electron acceptor shown in Table 2 were heated for 1,
The mixture was made into a saturated solution of 1,2-trichloroethane, cooled, and the precipitate deposited was collected to obtain a charge transfer complex. Table 2 shows the physical properties of the electron acceptor used and the charge transfer complex obtained. The meanings of the electron acceptor abbreviations in the table are as follows.
ＴＣＮＱ ：テトラシアノキノジメタン。TCNQ: Tetracyanoquinodimethane.
ＴＣＮＱＦ、： ２，３．５．６−テトラフルオロ−７
．７゜８．８〜テトラシアノキノジメタン、ＤＭＴＣＮ
Ｑ：２，５〜ジメチル−７、７，８，８−テトラシアノ
キノジメタン、 ＴＮＡＰ ： １１，１１，１２．１
２−テトラシアノ−２，６−ナフトキノジメタン、ＴＣ
ＮＥ：テトラシアノエチレン、ＤＤＱ：ジシアノジクロ
ロベンゾキノン、Ｉ３ ：テトラブチルアンモニウムト
リョーダイドから調製したもの。TCNQF: 2,3.5.6-tetrafluoro-7
．． 7°8.8 ~ Tetracyanoquinodimethane, DMTCN
Q: 2,5-dimethyl-7,7,8,8-tetracyanoquinodimethane, TNAP: 11,11,12.1
2-tetracyano-2,6-naphthoquinodimethane, TC
NE: prepared from tetracyanoethylene, DDQ: dicyanodichlorobenzoquinone, I3: tetrabutylammonium triodide.
以上の結果より、化合物（１）を電子供与体としこれと
他成分の電子受容体で形成される電荷移動錯体がＴＳｅ
Ｔを電子供与体とするものより優れた導電性を有するこ
とが分る。From the above results, it is clear that the charge transfer complex formed by compound (1) as an electron donor and other components as electron acceptors is TSe.
It can be seen that the conductivity is superior to that in which T is used as an electron donor.
（以下余白）(Margin below)
Claims (7)
２−ｃｄ：４，５−ｃ′ｄ′］ビス［１，２］ジセレノ
ール。 ▲数式、化学式、表等があります▼（ I ）(1) Naphthaceno [1,1
2-cd:4,5-c'd']bis[1,2]diselenol. ▲There are mathematical formulas, chemical formulas, tables, etc.▼(I)
トラクロロナフタセン。 ▲数式、化学式、表等があります▼（II）(2) 1,4,5,12-tetrachloronaphthacene represented by the following formula (II). ▲There are mathematical formulas, chemical formulas, tables, etc.▼(II)
２，１２−ヘキサクロロ−５，１２−ジヒドロナフタセ
ン。 ▲数式、化学式、表等があります▼（III）(3) 1,4,5,5,1 represented by the following formula (III)
2,12-hexachloro-5,12-dihydronaphthacene. ▲There are mathematical formulas, chemical formulas, tables, etc.▼(III)
，１２−ジヒドロキシ−１，４−ナフタセンキノン。 ▲数式、化学式、表等があります▼（IV）(4) 2,3-dihydro-5 represented by the following formula (IV)
, 12-dihydroxy-1,4-naphthacenequinone. ▲There are mathematical formulas, chemical formulas, tables, etc.▼(IV)
，５−ｃ′ｄ′］ビス［１，２］ジセレノールを電子供
与体とし、他成分の電子受容体とから導かれた電荷移動
錯体。(5) Naphthaceno [1,12-cd:4 according to claim 1]
, 5-c'd']bis[1,2]diselenol as an electron donor and a charge transfer complex derived from other components as electron acceptors.
ジメタン、２，３，５，６−テトラフルオロ−７、７，
８，８−テトラシアノキノジメタン、２，５−ジメチル
−７、７，８，８−テトラシアノキノジメタン、１１，
１１，１２，１２−テトラシアノ−２、６−ナフトキノ
ジメタン、２，３−ジクロロ−５、６−ジシアノベンゾ
キノン、１，１，２，３，４，４−ヘキサシアノブタジ
エン、テトラシアノエチレン、ジクロロジシアノベンゾ
キノン、クロラニル、ブロモアニル、塩素、臭素、ヨウ
素又はトリヨーダイドのいずれかである請求項５記載の
電荷移動錯体。(6) The electron acceptor is 7,7,8,8-tetracyanoquinodimethane, 2,3,5,6-tetrafluoro-7,7,
8,8-tetracyanoquinodimethane, 2,5-dimethyl-7,7,8,8-tetracyanoquinodimethane, 11,
11,12,12-tetracyano-2,6-naphthoquinodimethane, 2,3-dichloro-5,6-dicyanobenzoquinone, 1,1,2,3,4,4-hexacyanobutadiene, tetracyanoethylene, dichloro The charge transfer complex according to claim 5, which is any one of dicyanobenzoquinone, chloranil, bromoanil, chlorine, bromine, iodine, or triiodide.
〜５である請求項５又は６記載の電荷移動錯体。(7) The molar ratio of electron donor and electron acceptor is 1:0.25
7. The charge transfer complex according to claim 5 or 6, wherein the charge transfer complex is .about.5.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP15844390A JPH0678300B2 (en) | 1990-06-15 | 1990-06-15 | Novel tetraselenotetracene and its complex |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP15844390A JPH0678300B2 (en) | 1990-06-15 | 1990-06-15 | Novel tetraselenotetracene and its complex |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH0449274A true JPH0449274A (en) | 1992-02-18 |
| JPH0678300B2 JPH0678300B2 (en) | 1994-10-05 |
Family
ID=15671882
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP15844390A Expired - Lifetime JPH0678300B2 (en) | 1990-06-15 | 1990-06-15 | Novel tetraselenotetracene and its complex |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0678300B2 (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5624510A (en) * | 1992-02-25 | 1997-04-29 | Cca Inc. | Method for producing patterned shaped article |
| WO1998010170A1 (en) | 1996-09-03 | 1998-03-12 | Hitachi Construction Machinery Co., Ltd. | Tunnel excavation method and tunnel excavator |
| JP2006199682A (en) * | 2004-12-14 | 2006-08-03 | Mitsubishi Chemicals Corp | Polyacene compound and method for producing the same, and organic electronic device using the same |
| CN102295562A (en) * | 2011-07-01 | 2011-12-28 | 中国科学院微生物研究所 | Antineoplastic compound, its preparation method and applications |
-
1990
- 1990-06-15 JP JP15844390A patent/JPH0678300B2/en not_active Expired - Lifetime
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5624510A (en) * | 1992-02-25 | 1997-04-29 | Cca Inc. | Method for producing patterned shaped article |
| WO1998010170A1 (en) | 1996-09-03 | 1998-03-12 | Hitachi Construction Machinery Co., Ltd. | Tunnel excavation method and tunnel excavator |
| US6142577A (en) * | 1996-09-03 | 2000-11-07 | Hitachi Construction Machinery Co., Ltd. | Hydraulic muck handling system for tunnel boring machine |
| JP2006199682A (en) * | 2004-12-14 | 2006-08-03 | Mitsubishi Chemicals Corp | Polyacene compound and method for producing the same, and organic electronic device using the same |
| CN102295562A (en) * | 2011-07-01 | 2011-12-28 | 中国科学院微生物研究所 | Antineoplastic compound, its preparation method and applications |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0678300B2 (en) | 1994-10-05 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Yui et al. | Novel electron acceptors bearing a heteroquinonoid system. I. Synthesis and conductive complexes of 5, 5'-bis (dicyanomethylene)-5, 5'-dihydro-. DELTA. x (x= 2, 2')-bithiophene and related compounds. | |
| Larsen et al. | 1, 3, 5, 7-Tetrathia-s-indacene-2, 6-dione chemistry. Synthesis of new multisulfur donor molecules and nickel-dithiolene electron-transfer complexes | |
| Barbon et al. | Synthesis and characterization of conjugated/cross-conjugated benzene-bridged boron difluoride formazanate dimers | |
| Razus et al. | 1-Phenylselanylazulenes: synthesis and selenium atom oxidation | |
| JP2003500510A (en) | New subphthalocyanine colorant, ink composition, and method for producing the same | |
| JP5193218B2 (en) | Novel highly conductive organic charge carrier transport material | |
| Ishida et al. | Novel electron acceptors bearing a heteroquinonoid system. III: 2, 5-bis (dicyanomethylene)-2, 5-dihydrofuran and its conjugated homologues as novel oxygen-containing electron acceptors. | |
| JPH0449274A (en) | Novel tetraselenotetracene and complex containing the same | |
| Román et al. | Synthesis and electrochemical properties of cavitands functionalized with 4, 4′-bipyridinium units | |
| Feliz et al. | Solid state synthesis, structure and optical limiting properties of seleno cuboidal clusters [M3Se4X3 (diphosphine) 3]+(M= Mo, W; X= Cl, Br) | |
| Otsubo et al. | 2, 3: 5, 6‐bis (ethylenedithio)‐and bis (trimethylenedithio)‐N, N′‐dicyanoquinonediimines as new electron acceptors | |
| Nowak et al. | Synthesis of novel heteropentacenes containing nitrogen, sulfur and oxygen or selenium | |
| JPH0680672A (en) | New electron acceptor and electrically conductive transfer complex containing the acceptor | |
| Mørkved et al. | Zn (quinoline) 2 Cl 2: an efficient reagent for synthesis of zinc azaphthalocyanines with thiomorpholine-or pyrazole substituents | |
| JPH0689001B2 (en) | Bis (octaalkyl phthalocyaninato) lanthanide compound | |
| EP4303210A1 (en) | Method for producing pentafluorosulfanyl group-containing aryl compound | |
| Piskunov et al. | Template Assembling of the Pentadentate Redox-Active Ligand in the Coordination Sphere of Tin (IV) | |
| Wegner et al. | Novel oligomeric TTF systems with extended conjugation | |
| JPH0653744B2 (en) | Alkyl cyanophthalocyanine compound | |
| Hachem et al. | Influence of bulky groups in single-component conductors based on neutral radical gold bis (dithiolene) complexes | |
| Wu et al. | First cycloruthenation of 2-alkenylpyridines: synthesis, characterization and properties | |
| JPS63225382A (en) | Novel benzoquinone derivative and production thereof | |
| JPH01100171A (en) | Production of phthalocyanine compound | |
| Byabartta | Sulphur-bridged ruthenium–molybdenum complexes:[(R-aapm) 2 Ru (μ-S) 2 Mo (OH) 2]. Synthesis, spectroscopic and electro-chemical characterization. R-AAPM= 2-(arylazo) pyrimidine | |
| JPS6317863A (en) | Tcnq complex |