Jump to main content
Jump to site search

Issue 23, 2018
Previous Article Next Article

ipso-Arylative polymerization as a route to π-conjugated polymers: synthesis of poly(3-hexylthiophene)

Author affiliations

Abstract

ipso-Arylative cross-coupling with two 3-hexylthiophene derivatives, (5-bromo-4-hexylthiophen-2-yl)diphenylmethanol and 2-(5-bromo-4-hexylthiophen-2-yl)propan-2-ol, has been used to prepare poly(3-hexylhiophene) (P3HT) as a model conjugated polymer. P3HT with number-average molecular weights ranging from 8–20 kg mol−1 (Đ 1.4–2.2) was prepared from 5-bromo-4-hexylthiophen-2-yl)diphenylmethanol with a Pd(OAc)2/PCy3/Cs2CO3 catalyst system. Only oligomerization of 2-(5-bromo-4-hexylthiophen-2-yl)propan-2-ol (Mn ≈ 3 kg mol−1) was observed under similar conditions. Studies with model compounds suggest that side reactions involving end-group loss limit ultimate molecular weights.

Graphical abstract: ipso-Arylative polymerization as a route to π-conjugated polymers: synthesis of poly(3-hexylthiophene)

Back to tab navigation

Supplementary files

Publication details

The article was received on 19 Apr 2018, accepted on 22 May 2018 and first published on 23 May 2018


Article type: Paper
DOI: 10.1039/C8PY00605A
Author version
available:

Download author version (PDF)
Polym. Chem., 2018,9, 3223-3231

  •   Request permissions

    ipso-Arylative polymerization as a route to π-conjugated polymers: synthesis of poly(3-hexylthiophene)

    F. Shih, S. Tian, N. Gallagher, Y. S. Park and R. B. Grubbs, Polym. Chem., 2018, 9, 3223
    DOI: 10.1039/C8PY00605A

Search articles by author

Spotlight

Advertisements