α,β-Unsubstituted meso-Positioning Thienyl BODIPY: A Promising Electron Deficient Building Block for the Development of Near Infrared (NIR) p-type Donor-Acceptor (D-A) Conjugated Polymers

Benedetta Squeo, Vasilis G. Gregoriou, Yang Han, Alex Palma-Cando, Sybille Allard, Efthymis Serpetzoglou, Ioannis Konidakis, Emmanuel Stratakis, Apostolos Avgeropoulos, Thomas D. Anthopoulos, Martin Heeney, Ullrich Scherf, Christos L. Chochos

Research output: Contribution to journalArticlepeer-review

18 Scopus citations

Abstract

It is demonstrated that α,β-unsubstituted meso-positioning thienyl BODIPY is an electron deficient unit that leads to the development of ultra low optical band gap (Egopt < 1 eV) π-conjugated D-A quarterthiophene polymers. Furthermore, it is revealed that the optoelectronic, electrochemical and charge transporting properties of the resulting α,β-unsubstituted meso-positioning thienyl BODIPY quaterthiophene-based polymers are alkyl side chain positioning dependent. Tail-to-tail (TT) positioning of the alkyl side chains at the two central thiophenes of the quaterthiophene segment results to lower Egopt, higher energy levels and increased hole mobility as compared to head-to-head (HH) positioning. Finally, even though the synthesized polymers exhibit high electron affinity, higher even to that of the fullerene derivative [6,6]-phenyl-C71-butyric acid methyl ester (PC71BM), they present only p-type behaviour in field effect transistors (FETs) independent to the alkyl side chain positioning.
Original languageEnglish (US)
Pages (from-to)4030-4040
Number of pages11
JournalJournal of Materials Chemistry C
Volume6
Issue number15
DOIs
StatePublished - 2018

Bibliographical note

KAUST Repository Item: Exported on 2020-10-01
Acknowledgements: This project has received funding from the European Community’s Seventh Framework Programme (FP7/2007-2013) under the Grant Agreement n° 331389 project ECOCHEM, n° 607585 project OSNIRO and no 604603 project MatHero. The authors would like to thank Anke Helfer from BUW for the mass spectrometry measurements.

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