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Synlett 2018; 29(19): 2572-2576
DOI: 10.1055/s-0037-1609949
cluster
© Georg Thieme Verlag Stuttgart · New York

Electron Acceptors Based on Cyclopentannulated Tetracenes

Gajanan C. Kulkarni
,
Jean L. Morales-Cruz
,
Waseem A. Hussain
,
Ian J. Garvey
,
Kyle N. Plunkett*
Department of Chemistry and Biochemistry, Southern Illinois University, Carbondale, IL 62901, USA   Email: kplunkett@chem.siu.edu
› Author AffiliationsWe are grateful to the National Science Foundation (NSF CAREER CHE-#1352431) for financial support. J.L.M.-C. was supported by NSF REU grant DMR-#1757954
Further Information

Publication History

Received: 01 August 2018

Accepted after revision: 19 August 2018

Publication Date:
11 September 2018 (online)

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Published as part of the Cluster Synthesis of Materials

Abstract

New cyclopenta-fused polycyclic aromatic hydrocarbons (CP-PAHs) based on tetracene have been prepared by a palladium-catalyzed cyclopentannulation reaction. The new compounds have low-energy lowest unoccupied molecular orbitals (LUMOs) and relatively small band gaps. The photooxidative stability was intermediate to previously prepared CP-PAHs based on anthracene and pentacene as found in traditional acene stabilities. Scholl cyclodehydrogenation of pendant aryl groups led to materials that quickly formed endoperoxide products.

Key words

cyclopenta-fused polycyclic aromatic hydrocarbons - electron acceptors - acenes - palladium-catalyzed annulation

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1609949.
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  • References and Notes

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