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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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Publication details

The article was received on 10 Sep 2018, accepted on 23 Nov 2018 and first published on 23 Nov 2018


Article type: Communication
DOI: 10.1039/C8CC07327A
Citation: Chem. Commun., 2018,54, 14140-14143
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    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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