Reliable suzuki chemistry for functionalised polythiophene synthesis

Simon J. Higgins; Iain Liversedge; Samer Badriya; Martin Heeney; Mark Giles; Lain McCulloch

doi:10.1557/proc-1003-o01-06

Reliable suzuki chemistry for functionalised polythiophene synthesis

Simon J. Higgins, Iain Liversedge, Samer Badriya, Martin Heeney, Mark Giles, Lain McCulloch

Research output: Chapter in Book/Report/Conference proceeding › Conference contribution

Abstract

Until recently, the synthesis of polythiophenes using Suzuki chemistry has proven difficult because of the ready protodeborylation of thiophene boronates. However, we now report that the new generation of bulky, electron-rich Pd(O)-phosphane catalysts are effective and reliable for the preparation of regioregular polyalkylthiophenes using Suzuki coupling. Moreover, the monomers can be prepared in high yield by Ir-catalysed borylation, without the need for strong organolithium bases, making this potentially a highly functional group-tolerant approach to polyalkylthiophene derivatives. Perfluoroalkylthiophenes also undergo this reaction.

Original language	English (US)
Title of host publication	Materials Research Society Symposium Proceedings - Organic Thin-Film Electronics- Materials, Processes, and Applications
Publisher	Materials Research Society
Pages	1-6
Number of pages	6
ISBN (Print)	9781605604367
DOIs	https://doi.org/10.1557/proc-1003-o01-06
State	Published - 2007
Externally published	Yes
Event	Organic Thin-Film Electronics- Materials, Processes, and Applications - 2007 MRS Spring Meeting - San Francisco, CA, United States Duration: Apr 9 2007 → Apr 13 2007

Publication series

Name	Materials Research Society Symposium Proceedings
Volume	1003
ISSN (Print)	0272-9172

Conference

Conference	Organic Thin-Film Electronics- Materials, Processes, and Applications - 2007 MRS Spring Meeting
Country/Territory	United States
City	San Francisco, CA
Period	4/9/07 → 4/13/07

All Science Journal Classification (ASJC) codes

General Materials Science
Condensed Matter Physics
Mechanics of Materials
Mechanical Engineering

Access to Document

10.1557/proc-1003-o01-06

Cite this

Higgins, S. J., Liversedge, I., Badriya, S., Heeney, M., Giles, M., & McCulloch, L. (2007). Reliable suzuki chemistry for functionalised polythiophene synthesis. In Materials Research Society Symposium Proceedings - Organic Thin-Film Electronics- Materials, Processes, and Applications (pp. 1-6). (Materials Research Society Symposium Proceedings; Vol. 1003). Materials Research Society. https://doi.org/10.1557/proc-1003-o01-06

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abstract = "Until recently, the synthesis of polythiophenes using Suzuki chemistry has proven difficult because of the ready protodeborylation of thiophene boronates. However, we now report that the new generation of bulky, electron-rich Pd(O)-phosphane catalysts are effective and reliable for the preparation of regioregular polyalkylthiophenes using Suzuki coupling. Moreover, the monomers can be prepared in high yield by Ir-catalysed borylation, without the need for strong organolithium bases, making this potentially a highly functional group-tolerant approach to polyalkylthiophene derivatives. Perfluoroalkylthiophenes also undergo this reaction.",

author = "Higgins, {Simon J.} and Iain Liversedge and Samer Badriya and Martin Heeney and Mark Giles and Lain McCulloch",

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Higgins, SJ, Liversedge, I, Badriya, S, Heeney, M, Giles, M & McCulloch, L 2007, Reliable suzuki chemistry for functionalised polythiophene synthesis. in Materials Research Society Symposium Proceedings - Organic Thin-Film Electronics- Materials, Processes, and Applications. Materials Research Society Symposium Proceedings, vol. 1003, Materials Research Society, pp. 1-6, Organic Thin-Film Electronics- Materials, Processes, and Applications - 2007 MRS Spring Meeting, San Francisco, CA, United States, 4/9/07. https://doi.org/10.1557/proc-1003-o01-06

Reliable suzuki chemistry for functionalised polythiophene synthesis. / Higgins, Simon J.; Liversedge, Iain; Badriya, Samer et al.
Materials Research Society Symposium Proceedings - Organic Thin-Film Electronics- Materials, Processes, and Applications. Materials Research Society, 2007. p. 1-6 (Materials Research Society Symposium Proceedings; Vol. 1003).

Research output: Chapter in Book/Report/Conference proceeding › Conference contribution

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T1 - Reliable suzuki chemistry for functionalised polythiophene synthesis

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AB - Until recently, the synthesis of polythiophenes using Suzuki chemistry has proven difficult because of the ready protodeborylation of thiophene boronates. However, we now report that the new generation of bulky, electron-rich Pd(O)-phosphane catalysts are effective and reliable for the preparation of regioregular polyalkylthiophenes using Suzuki coupling. Moreover, the monomers can be prepared in high yield by Ir-catalysed borylation, without the need for strong organolithium bases, making this potentially a highly functional group-tolerant approach to polyalkylthiophene derivatives. Perfluoroalkylthiophenes also undergo this reaction.

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Higgins SJ, Liversedge I, Badriya S, Heeney M, Giles M, McCulloch L. Reliable suzuki chemistry for functionalised polythiophene synthesis. In Materials Research Society Symposium Proceedings - Organic Thin-Film Electronics- Materials, Processes, and Applications. Materials Research Society. 2007. p. 1-6. (Materials Research Society Symposium Proceedings). doi: 10.1557/proc-1003-o01-06

Reliable suzuki chemistry for functionalised polythiophene synthesis

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