Helically Locked Tethered Twistacenes

Anjan Bedi, Linda J.W. Shimon, Ori Gidron*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

54 Scopus citations

Abstract

Twisting linear acenes out of planarity affects their electronic and optical properties, and induces chirality. However, it is difficult to isolate the effect of twisting from the substituent effect. Moreover, many twistacenes (twisted acenes) readily racemize in solution. Here, we introduce a series of twistacenes having an anthracene backbone diagonally tethered by an n-alkyl bridge, which induces a twist of various angles. This allows us to systematically monitor the effect of twisting on electronic and optical properties. We find that absorption is bathochromically shifted with increasing twist, while fluorescence quantum efficiency drops dramatically. The tethered twistacenes were isolated to their enantiomerically pure form, displaying strong chiroptical properties and anisotropy factor (g-value). No racemization was observed even upon prolonged heating, rendering these tethered twistacenes suitable as enantiopure helical building units for π-conjugated backbones.

Original languageAmerican English
Pages (from-to)8086-8090
Number of pages5
JournalJournal of the American Chemical Society
Volume140
Issue number26
DOIs
StatePublished - 5 Jul 2018

Bibliographical note

Publisher Copyright:
© Copyright 2018 American Chemical Society.

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