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Synlett 2018; 29(19): 2499-2502
DOI: 10.1055/s-0037-1610163
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© Georg Thieme Verlag Stuttgart · New York

A Heptacyclic Heptacycle: A Doubly Naphtho[b]thiophene Fused Borepin

Reid E. Messersmith
a   Department of Chemistry, Johns Hopkins University, 3400 North Charles Street, Baltimore, Maryland 21218, USA   Email: tovar@jhu.edu
,
Maxime A. Siegler
a   Department of Chemistry, Johns Hopkins University, 3400 North Charles Street, Baltimore, Maryland 21218, USA   Email: tovar@jhu.edu
,
John D. Tovar*
a   Department of Chemistry, Johns Hopkins University, 3400 North Charles Street, Baltimore, Maryland 21218, USA   Email: tovar@jhu.edu
b   Department of Materials Science and Engineering, Johns Hopkins University, 3400 North Charles Street, Baltimore, Maryland 21218, USA
› Author AffiliationsThis research was supported by the National Science Foundation (CHE-1464798). R.E.M. was the recipient of a William Hooper Grafflin fellowship administered by Johns Hopkins University.
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Publication History

Received: 03 April 2018

Accepted after revision: 08 May 2018

Publication Date:
12 June 2018 (online)

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Published as part of the Cluster Synthesis of Materials

Abstract

The synthesis and characterization of a doubly naphtho[b]thiophene fused borepin is reported herein, and the properties are compared to smaller benzo[b]thiophene and thiophene fused borepins. The synthesis involved the preparation of a symmetrical disubstituted alkyne that was reduced to a Z-olefin. This was followed by borepin formation from the alkene directly by way of thieno dilithiation. The electronic properties are consistent with extended benzannulation of the smaller analogues, and the enhancement of the brickwork type stacking is apparent as planar aromatic wings are extended from the central borepin core.

Key words

π-conjugation - borepins - aromaticity - organic electronics - boron

Supporting Information

    Copies of experimental details, proposed nomenclature, CV, 1H NMR and 13C NMR spectroscopy. X-ray crystallographic data for compound 3 in chloroform/methanol (CCDC: 1833288) ortho-dichlorobenzene (CCDC: 1833289). Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1610163.
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