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

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ipso-Arylative polymerization as a route to π-conjugated polymers: synthesis of poly(3-hexylthiophene)†
Polymer Chemistry ( IF 4.1 ) Pub Date : 2018-05-23 00:00:00 , DOI: 10.1039/c8py00605a
Feng-Yang Shih _{1,

2,

3,

4} , Sisi Tian _{1,

2,

3,

4} , Nicholas Gallagher _{1,

2,

3,

4} , Young S. Park _{4,

5,

6,

7} , Robert B. Grubbs _{1,

2,

3,

4}

Affiliation

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 (M_n ≈ 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.

中文翻译：

本位-Arylative聚合以π共轭聚合物的路线：聚（3-己基噻吩）的合成†

本位-Arylative具有两个3己基噻吩衍生物交叉耦合，（5-溴-4-己基噻吩-2-基）二苯基甲醇和2-（5-溴-4-己基噻吩-2-基）丙-2-醇，具有用于制备聚（3-己基噻吩）（P3HT）的模型共轭聚合物。P3HT与数均分子量为8-20公斤摩尔^-1（Đ 1.4-2.2），从5-溴-4-己基噻吩-2-基）与钯（OAC二苯基甲醇）中制备₂ / PCY ₃ / CS ₂ CO ₃催化剂体系。2-（5-溴-4-己基噻吩-2-基）丙-2-醇（仅低聚中号_Ñ ≈3公斤摩尔^-1）是在类似条件下观察到的。对模型化合物的研究表明，涉及端基损失的副反应限制了最终分子量。

更新日期：2018-05-23

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