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Short Paper | Special issue | Vol 97, No. 2, 2018, pp.1313-1318
Published online, 8th June, 2018
DOI: 10.3987/COM-18-S(T)92
Polymorphism of Macrocyclic Oligothiophehe 8-Mers

Hideyuki Shimizu, Tahmina Haque, Masataka Takashika, Hiroyuki Otani, and Masahiko Iyoda*

*Department of Chemistry, Graduate School of Science and Engineering, Tokyo Metropolitan University, Hachioji, Tokyo 192-0397, Japan

Abstract

Macrocyclic oligothiophene 8-mer E,E-8T6A composed of eight thienylene, six ethynylene, and two vinylene units exhibits unique polymorphism. In the solid state, E,E-8T6A formed nanostructured polymorphs such as single crystals, fibers, long and short rods, and square tubes depending on the solvent used for crystallization. In contrast, E-8T7A with one vinylene unit and 8T8A without vinylene unit afforded single crystals, microcrystalline, and short rods in the solid state. Morphological difference between E,E-8T6A and E-8T7A/8T8A is due to the flexibility of the macroring of E,E-8T6A with two vinylene units, and the shape-persistent but rather flexible E,E-8T6A forms various polymorphs in the solid state.