4.7 Article

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

期刊

POLYMER CHEMISTRY
卷 9, 期 23, 页码 3223-3231

出版社

ROYAL SOC CHEMISTRY
DOI: 10.1039/c8py00605a

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资金

  1. National Science Foundation [CHE-1506822]
  2. Division Of Chemistry
  3. Direct For Mathematical & Physical Scien [1506822] Funding Source: National Science Foundation

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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) (D 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 (M-n approximate to 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.

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