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Issue 100, 2018
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Cyclopentannulation and cyclodehydrogenation of isomerically pure 5,11-dibromo-anthradithiophenes leading to contorted aromatics

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Abstract

Isomerically pure 5,11-dibromo-2,8-dihexylanthra[2,3-b:76-b′]dithiophene, a brominated analog of anthracenedithiophene (ADT), was prepared and utilized for a palladium catalyzed cyclopentannulation reaction with 3,3′-dimethoxy-phenylacetylene to give cyclopentannulated ADT (CP-ADTs). A further Scholl cyclodehydrogenation reaction gave contorted aromatics with large splay angles, low optical gaps, and low LUMOs.

Graphical abstract: Cyclopentannulation and cyclodehydrogenation of isomerically pure 5,11-dibromo-anthradithiophenes leading to contorted aromatics

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Article information


Submitted
10 Sep 2018
Accepted
23 Nov 2018
First published
23 Nov 2018

Chem. Commun., 2018,54, 14140-14143
Article type
Communication
Author version available

Cyclopentannulation and cyclodehydrogenation of isomerically pure 5,11-dibromo-anthradithiophenes leading to contorted aromatics

S. R. Bheemireddy, W. A. Hussain, A. Uddin, Y. Du, M. P. Hautzinger, P. V. Kevorkian, F. A. Petrie and K. N. Plunkett, Chem. Commun., 2018, 54, 14140
DOI: 10.1039/C8CC07327A

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