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CC BY-NC-ND 4.0 · Organic Materials 2021; 03(02): 155-167
DOI: 10.1055/s-0041-1726450
Focus Issue: Peter Bäuerle 65th Birthday
Review

S,N-Heteropentacenes – Syntheses of Electron-Rich Anellated Pentacycles

Henning R. V. Berens
a   Institut für Organische Chemie und Makromolekulare Chemie, Heinrich-Heine-Universität Düsseldorf, Universitätsstraße 1, D-40225 Düsseldorf, Germany
,
Thomas J. J. Müller
a   Institut für Organische Chemie und Makromolekulare Chemie, Heinrich-Heine-Universität Düsseldorf, Universitätsstraße 1, D-40225 Düsseldorf, Germany
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Abstract

This review summarizes syntheses of S,N-heteropentacenes, i.e. electron-rich sulfur and nitrogen-embedding pentacycles, and briefly highlights selected applications in molecular electronics. Depending on the anellation mode and the number of incorporated heteroatoms, electron density can be raised by increasing nitrogen incorporation and polarizability is manifested by the sulfur content. In comparison to triacene analogues, the conjugation pathways of S,N-heteropentacenes are increased and the favorable acene-typical crystallization behavior allows for diverse application in organic electronics. Furthermore, substitution patterns allow fine-tuning the electronic properties, extending the π-systems, and supplying structural elements for further application.

1 Introduction

2 Thiophene-Centered S,N-Heteropentacenes

2.1 Dipyrrolo-Fused Thiophenes

2.2 Diindolo-Fused Thiophenes

3 Pyrrole-Centered S,N-Heteropentacenes

3.1 Dithieno-Fused Pyrroles

3.2 Bis[1]benzothieno-Fused Pyrrole

4 Fused 1,4-Thiazines

4.1 Dinaphtho-Fused 1,4-Thiazines

4.2 Bis[1]benzothieno-Fused 1,4-Thiazines

5 Conclusions and Outlook

Key words

heteroacenes - cross-coupling - condensations - cyclizations - modular syntheses - optoelectronics - energy conversion - materials

Dedicated to Prof. Dr. Peter Bäuerle on the occasion of his 65th birthday.




Publication History

Received: 29 January 2021

Accepted: 25 February 2021

Article published online:
01 April 2021

© 2021. The Author(s). This is an open access article published by Thieme under the terms of the Creative Commons Attribution-NonDerivative-NonCommercial License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes, or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by-nc-nd/4.0/)

Georg Thieme Verlag KG
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