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Synlett 2018; 29(19): 2529-2534
DOI: 10.1055/s-0037-1610286
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© Georg Thieme Verlag Stuttgart · New York

Synthesis and Photophysical Properties of Hexaphenylbenzene–Pyrrolo[3,2-b]pyrroles

Rafał Stężycki
a   Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44-52, 01-224 Warsaw, Poland   Email: dtgryko@icho.edu.pl
b   Warsaw University of Technology, Faculty of Chemistry, Noakowskiego 3, 00-664 Warsaw, Poland
,
David Reger
c   Department of Chemistry and Pharmacy and Interdisciplinary Center for Molecular Materials, Friedrich-Alexander-Universität Erlangen-Nürnberg, 91058 Erlangen, Germany   Email: norbert.jux@fau.de
,
Helen Hoelzel
c   Department of Chemistry and Pharmacy and Interdisciplinary Center for Molecular Materials, Friedrich-Alexander-Universität Erlangen-Nürnberg, 91058 Erlangen, Germany   Email: norbert.jux@fau.de
,
Norbert Jux*
c   Department of Chemistry and Pharmacy and Interdisciplinary Center for Molecular Materials, Friedrich-Alexander-Universität Erlangen-Nürnberg, 91058 Erlangen, Germany   Email: norbert.jux@fau.de
,
Daniel T. Gryko  *
a   Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44-52, 01-224 Warsaw, Poland   Email: dtgryko@icho.edu.pl
› Author AffiliationsThe authors would like to thank the Foundation for Polish Science (Grant TEAM/2016-3/22) and Global Research Laboratory Program (2014K1A1A2064569) through the National Research Foundation (NRF) funded by the Ministry of Science, ICT & Future Planning (Korea). N.J, H.H., and D. R. gratefully acknowledge support from the Deutsche Forschungsgemeinschaft via SFB 953 ‘Synthetic Carbon Allotropes’; D.R. acknowledges support from the Graduate School Molecular Science.
Further Information

Publication History

Received: 27 August 2018

Accepted after revision: 29 August 2018

Publication Date:
26 September 2018 (online)

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Published as part of the Cluster Synthesis of Materials

Abstract

Methods for the synthesis of pyrrolo[3,2-b]pyrroles containing hexaphenylbenzene moieties at the 2- and 5-positions or the 1- and 4-positions have been developed. It was shown that placing a hexaphenylbenzene moiety at the 2- and 5-positions requires a Diels–Alder reaction between an alkyne-substituted pyrrolopyrrole core and a 2,3,4,5-tetraphenylcyclopenta-2,4-dien-1-one. The resulting dyes show a strong blue fluorescence that was hypsochromically shifted by chlorination at the 3- and 6-positions. The overall conjugation between the hexaphenylbenzene moieties and the pyrrolopyrrole core is limited, as evident from their photophysical properties. The hexaphenylbenzene moieties attached to the pyrrolo[3,2-b]pyrrole core could not be transformed into hexa-peri-hexabenzocoronenes through intramolecular oxidative aromatic coupling.

Key words

chromophores - pyrrolopyrroles - halogenation - multicomponent reaction - hexaphenylbenzene - fluorescence

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1610286.
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