Synlett 2019; 30(10): 1111-1124
DOI: 10.1055/s-0037-1611739
account
© Georg Thieme Verlag Stuttgart · New York

Thiadiazoloquinoxalines

Ben-Lin Hu
,
Max Planck Institute for Polymer Research, Ackermannweg 10, 55128 Mainz, Germany   Email: martin.baumgarten@mpip-mainz.mpg.de
› Author Affiliations
We thank the Deutsche Forschungsgemeinschaft (8DFG) and SFB-TR49 for financial support. Ben-Lin Hu gratefully acknowledges the Alexander von Humboldt Stiftung for granting a research fellowship.
Further Information

Publication History

Received: 08 January 2019

Accepted after revision: 29 January 2019

Publication Date:
12 March 2019 (online)


Abstract

In this account we summarized our work on the modification and extension of the thiadiazoloquinoxaline (TQ) as a strong acceptor unit for organic electronics. While also alternating conjugated copolymers with different donors were published, the focus here is the description of variation of the acceptor unit leading to many small molecules with different electronic properties as indicated from their optical absorptions, cyclic voltammetry (CV) data, density functional theory (DFT), and time-dependent (TD-DFT) calculations. The extension with ortho-diquinones seemed a promising way to enlarge the TQ molecules and further increase their electron affinity. At the end it is demonstrated how these units can be merged with other acceptors like naphthalenediimide (NDI) and be extended in an iterative way to extremely long condensed pyrene-fused heteroacenes with TQ end groups just by ring opening of the thiadiazole five-membered ring followed by further condensations in an iterative way.

1 Introduction

2 The Synthesis of TQ Cores

3 The Extension of TQ

3.1 The Extension at 4,9-Positions

3.2 The Extension at 6,7-Positions

3.3 The Extension on NDI

3.4 The Extension with TQ for Endcapping (Bis TQ)

4 Conclusions

 
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