Triptycene End-Capped Benzothienobenzothiophene and Naphthothienobenzothiophene

Chemistry. 2020 Oct 1;26(55):12596-12605. doi: 10.1002/chem.202001125. Epub 2020 Sep 11.

Abstract

Previously it was demonstrated that triptycene end-capping can be used as a crystal engineering strategy to direct the packing of quinoxalinophenanthrophenazines (QPPs) towards cofacially stacked π dimers with large molecular overlap resulting in high charge transfer integrals. Remarkably, this packing motif was formed under different crystallization conditions and with a variety of derivatives bearing additional functional groups or aromatic substituents. Benzothienobenzothiophene (BTBT) and its derivatives are known as some of the best performing compounds for organic field-effect transistors. Here, the triptycene end-capping concept is introduced to this class of compounds and polymorphic crystal structures are investigated to evaluate the potential of triptycene end-caps as synthons for crystal engineering.

Keywords: benzothienobenzothiophene; charge transfer; crystal engineering; triptycene.