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Issue 12, 2022

Alkyl substituent-dependent systematic change in cold crystallization of azo molecules

Abstract

The thermal behavior of alkyl-derivatized 1-(2,4-dimethylphenylazo)-4-naphthol and 1-(2,4-dimethylphenylazo)-2-naphthol (2,4-DM-4-Cn and 2,4-DM-2-Cn, respectively) was investigated. The change in the position of the alkyl substituent led to a variation in the thermal behavior, including the cold crystallization, which is a heat-storing phenomenon. In addition, a comprehensive study of the alkyl chain length revealed that 2,4-DM-4-Cn had better crystallinity and exhibited cold crystallization with short alkyl chains. The π–π, C–H⋯N, and C–H⋯π interactions stabilized the crystal structure of 2,4-DM-4-Cn. On the other hand, the polymorphism of 2,4-DM-2-Cn inhibited the formation of a uniform crystalline phase during cooling, which led to poor crystallinity. The only difference between the compounds, the position of the substituent, resulted in a clear variation in the cold crystallization and heat storage properties.

Graphical abstract: Alkyl substituent-dependent systematic change in cold crystallization of azo molecules

Supplementary files

Article information

Article type
Paper
Submitted
13 Feb 2022
Accepted
25 Feb 2022
First published
02 Mar 2022
This article is Open Access
Creative Commons BY-NC license

RSC Adv., 2022,12, 7229-7236

Alkyl substituent-dependent systematic change in cold crystallization of azo molecules

A. Honda, Y. Hibi, K. Matsumoto, M. Kawai and K. Miyamura, RSC Adv., 2022, 12, 7229 DOI: 10.1039/D2RA00942K

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