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Triptycene End‐Capped Benzothienobenzothiophene and Naphthothienobenzothiophene

Lucas Ueberricke, Julia Schwarz, Farhad Ghalami, Maik Matthiesen, Frank Röminger, Sven M. Elbert, Jana Zaumseil, Marcus Elstner, Michael Mastalerz

2020Chemistry - A European Journal12 citationsDOIOpen Access PDF

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.

Topics & Concepts

TriptyceneMaterials scienceNanotechnologySynthesis and Properties of Aromatic CompoundsOrganic Electronics and PhotovoltaicsOrganic Chemistry Cycloaddition Reactions
Triptycene End‐Capped Benzothienobenzothiophene and Naphthothienobenzothiophene | Litcius