Download PDF
Synlett 2013; 24(8): 920-937
DOI: 10.1055/s-0032-1317804
Account
© Georg Thieme Verlag Stuttgart · New York

Dithieno[3,2-b:2′,3′-d]phospholes: A Look Back at the First Decade

Carlos Romero-Nieto*
a   Organisch-Chemisches Institut, Universität Heidelberg, Im Neuenheimer Feld 270, 69120 Heidelberg, Germany   Email: carlos.romero.nieto@oci.uni-heidelberg.de
,
Thomas Baumgartner*
b   Department of Chemistry, University of Calgary, 2500 University Drive NW, Calgary AB T2N 1N4, Canada   Fax: +1(403)2899488   Email: thomas.baumgartner@ucalgary.ca
› Author Affiliations
Further Information

Publication History

Received: 08 February 2013

Accepted: 13 March 2013

Publication Date:
11 April 2013 (online)

    Permissions and Reprints All articles of this category


Abstract

In this account, we describe our efforts in developing the chemistry of the highly luminescent dithieno[3,2-b:2′,3′-d]phosphole system over the last ten years. We provide an overview of the synthetic possibilities and the inherent tunability of the emission properties offered by this particular heterole.

1 Introduction

2 Synthesis and Properties of Dithieno[3,2-b:2′,3′-d]phospholes

3 Functionalization of Dithieno[3,2-b:2′,3′-d]phospholes

3.1 Phosphorus Functionalization

3.2 Functionalization at the 2- and 6-Positions

3.2.1 Symmetric Functionalization

3.2.2 Asymmetric Functionalization

3.3 Incorporation of Fused Rings onto the Main Scaffold

4 Photophysical Properties

5 Conclusions

Keywords

phosphorus - heterocycles - chromophores - polycycles - substituent effects - chemoselectivity.