Synthesis of terminally dendronized poly(3-hexylthiophene)s as a platform for functional conjugated polymers

Nobuhiro Watanabe; Clayton Mauldin; Jean M.J. Fréchet

doi:10.1021/ma071479j

Synthesis of terminally dendronized poly(3-hexylthiophene)s as a platform for functional conjugated polymers

Nobuhiro Watanabe, Clayton Mauldin, Jean M.J. Fréchet^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

11 Scopus citations

Abstract

A strategy for the synthesis of block copolymers consisting of regioregular poly(3-hexylthiophene) (RR-P3HT) with dendrons attached at on terminus of the poly(3-hexylthiophene) (P3HT). Peripheral hydroxy groups were end-capped by long-chain alkyl (mynstic) esters, while the focal point was activated with a 4-nitrophenyl ester for coupling to a reactive terminus of P3HT. RR-P3HT was prepared from 2-bromo-3-hexyl-5-iodothiophene (4) through the Grignard metathesis (GRIM) reaction. Polymerization via GRIM affords highly regioregular (RR) P3HT with a 5-bromothiophene end group. Detailed characterization of the P3HT produced through GRIM and the reaction mechanism were also described. The dendritic structure at the P3HT terminus can be further fictionalized at the periphery to endow specific properties to the overall assembly. The unique structure of the terminally dendronized P3HT is useful not only for devices but also for applications involving properties such as adhesion.

Original language	English (US)
Pages (from-to)	6793-6795
Number of pages	3
Journal	Macromolecules
Volume	40
Issue number	19
DOIs	https://doi.org/10.1021/ma071479j
State	Published - Sep 18 2007
Externally published	Yes

ASJC Scopus subject areas

Organic Chemistry
Polymers and Plastics
Inorganic Chemistry
Materials Chemistry

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title = "Synthesis of terminally dendronized poly(3-hexylthiophene)s as a platform for functional conjugated polymers",

abstract = "A strategy for the synthesis of block copolymers consisting of regioregular poly(3-hexylthiophene) (RR-P3HT) with dendrons attached at on terminus of the poly(3-hexylthiophene) (P3HT). Peripheral hydroxy groups were end-capped by long-chain alkyl (mynstic) esters, while the focal point was activated with a 4-nitrophenyl ester for coupling to a reactive terminus of P3HT. RR-P3HT was prepared from 2-bromo-3-hexyl-5-iodothiophene (4) through the Grignard metathesis (GRIM) reaction. Polymerization via GRIM affords highly regioregular (RR) P3HT with a 5-bromothiophene end group. Detailed characterization of the P3HT produced through GRIM and the reaction mechanism were also described. The dendritic structure at the P3HT terminus can be further fictionalized at the periphery to endow specific properties to the overall assembly. The unique structure of the terminally dendronized P3HT is useful not only for devices but also for applications involving properties such as adhesion.",

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AU - Watanabe, Nobuhiro

AU - Mauldin, Clayton

AU - Fréchet, Jean M.J.

PY - 2007/9/18

Y1 - 2007/9/18

N2 - A strategy for the synthesis of block copolymers consisting of regioregular poly(3-hexylthiophene) (RR-P3HT) with dendrons attached at on terminus of the poly(3-hexylthiophene) (P3HT). Peripheral hydroxy groups were end-capped by long-chain alkyl (mynstic) esters, while the focal point was activated with a 4-nitrophenyl ester for coupling to a reactive terminus of P3HT. RR-P3HT was prepared from 2-bromo-3-hexyl-5-iodothiophene (4) through the Grignard metathesis (GRIM) reaction. Polymerization via GRIM affords highly regioregular (RR) P3HT with a 5-bromothiophene end group. Detailed characterization of the P3HT produced through GRIM and the reaction mechanism were also described. The dendritic structure at the P3HT terminus can be further fictionalized at the periphery to endow specific properties to the overall assembly. The unique structure of the terminally dendronized P3HT is useful not only for devices but also for applications involving properties such as adhesion.

AB - A strategy for the synthesis of block copolymers consisting of regioregular poly(3-hexylthiophene) (RR-P3HT) with dendrons attached at on terminus of the poly(3-hexylthiophene) (P3HT). Peripheral hydroxy groups were end-capped by long-chain alkyl (mynstic) esters, while the focal point was activated with a 4-nitrophenyl ester for coupling to a reactive terminus of P3HT. RR-P3HT was prepared from 2-bromo-3-hexyl-5-iodothiophene (4) through the Grignard metathesis (GRIM) reaction. Polymerization via GRIM affords highly regioregular (RR) P3HT with a 5-bromothiophene end group. Detailed characterization of the P3HT produced through GRIM and the reaction mechanism were also described. The dendritic structure at the P3HT terminus can be further fictionalized at the periphery to endow specific properties to the overall assembly. The unique structure of the terminally dendronized P3HT is useful not only for devices but also for applications involving properties such as adhesion.

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JO - Macromolecules

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ER -

Synthesis of terminally dendronized poly(3-hexylthiophene)s as a platform for functional conjugated polymers

Abstract

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