Synthesis and characterization of naphthalene diimide/diethynylbenzene copolymers

Tissa Sajoto; Shree Prakash Tiwari; Huifang Li; Chad Risko; Stephen Barlow; Qing Zhang; Jian Yang Cho; Jean Luc Brédas; Bernard Kippelen; Seth R. Marder

doi:10.1016/j.polymer.2012.01.016

Synthesis and characterization of naphthalene diimide/diethynylbenzene copolymers

Tissa Sajoto, Shree Prakash Tiwari, Huifang Li, Chad Risko, Stephen Barlow, Qing Zhang, Jian Yang Cho, Jean Luc Brédas, Bernard Kippelen, Seth R. Marder^*

^*Corresponding author for this work

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

25 Scopus citations

Abstract

A series of conjugated polymers has been synthesized by Sonogashira coupling of N,N′-bis(2-octyldodecyl)-2,6-dibromonaphthalene-1,4,5,8- bis(dicarboximide) and four para-diethynylbenzene derivatives: 1,4-diethynyl-2,5-dihexadecyloxybenzene, 1,4-diethynyl-2,5-bis(2- octyldodecyloxy) benzene, 1,4-bis(2-ethylhexyl)-2,5-diethynylbenzene, 1,4-diethynyl-2,5-bis(trifluoromethyl)benzene. The polymers display absorption maxima at wavelengths ranging from 530 nm to 654 nm with molar absorptivities ranging from ca. 4 to 7 × 10⁴ M^-1 cm^-1. The peak reduction potentials, determined by differential pulse voltammetry, for polymer films varied from -0.93 to -1.14 V vs. ferrocenium/ferrocene with the trifluoromethyl-substituted derivative being the most readily reduced. All four polymers exhibited electron transport characteristics in bottom-gate/top-contact field-effect transistors, showing average electron mobility values ranging from 1.4 × 10^-4 to 3.7 × 10^-3 cm² V^-1 s^-1.

Original language	English (US)
Pages (from-to)	1072-1078
Number of pages	7
Journal	Polymer
Volume	53
Issue number	5
DOIs	https://doi.org/10.1016/j.polymer.2012.01.016
State	Published - Feb 28 2012
Externally published	Yes

Bibliographical note

Funding Information:
We would like to acknowledge Benjamin Wunsch, Chun Huang, and Sergio Paniagua for acquiring TGA and DSC data. This work was funded by Solvay S.A., the Office of Naval Research , and the STC Program of the National Science Foundation ( DMR-0120967 ).

Keywords

Conjugated polymers
Electron transport
Naphthalene diimide polymers

ASJC Scopus subject areas

Organic Chemistry
Polymers and Plastics
Materials Chemistry

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10.1016/j.polymer.2012.01.016

Cite this

@article{5d798a69e029423a96bbc499e2e990ec,

title = "Synthesis and characterization of naphthalene diimide/diethynylbenzene copolymers",

abstract = "A series of conjugated polymers has been synthesized by Sonogashira coupling of N,N′-bis(2-octyldodecyl)-2,6-dibromonaphthalene-1,4,5,8- bis(dicarboximide) and four para-diethynylbenzene derivatives: 1,4-diethynyl-2,5-dihexadecyloxybenzene, 1,4-diethynyl-2,5-bis(2- octyldodecyloxy) benzene, 1,4-bis(2-ethylhexyl)-2,5-diethynylbenzene, 1,4-diethynyl-2,5-bis(trifluoromethyl)benzene. The polymers display absorption maxima at wavelengths ranging from 530 nm to 654 nm with molar absorptivities ranging from ca. 4 to 7 × 104 M-1 cm-1. The peak reduction potentials, determined by differential pulse voltammetry, for polymer films varied from -0.93 to -1.14 V vs. ferrocenium/ferrocene with the trifluoromethyl-substituted derivative being the most readily reduced. All four polymers exhibited electron transport characteristics in bottom-gate/top-contact field-effect transistors, showing average electron mobility values ranging from 1.4 × 10-4 to 3.7 × 10-3 cm2 V-1 s-1.",

keywords = "Conjugated polymers, Electron transport, Naphthalene diimide polymers",

author = "Tissa Sajoto and Tiwari, {Shree Prakash} and Huifang Li and Chad Risko and Stephen Barlow and Qing Zhang and Cho, {Jian Yang} and Br{\'e}das, {Jean Luc} and Bernard Kippelen and Marder, {Seth R.}",

note = "Funding Information: We would like to acknowledge Benjamin Wunsch, Chun Huang, and Sergio Paniagua for acquiring TGA and DSC data. This work was funded by Solvay S.A., the Office of Naval Research , and the STC Program of the National Science Foundation ( DMR-0120967 ). ",

year = "2012",

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day = "28",

doi = "10.1016/j.polymer.2012.01.016",

language = "English (US)",

volume = "53",

pages = "1072--1078",

journal = "Polymer",

issn = "0032-3861",

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T1 - Synthesis and characterization of naphthalene diimide/diethynylbenzene copolymers

AU - Sajoto, Tissa

AU - Tiwari, Shree Prakash

AU - Li, Huifang

AU - Risko, Chad

AU - Barlow, Stephen

AU - Zhang, Qing

AU - Cho, Jian Yang

AU - Brédas, Jean Luc

AU - Kippelen, Bernard

AU - Marder, Seth R.

N1 - Funding Information: We would like to acknowledge Benjamin Wunsch, Chun Huang, and Sergio Paniagua for acquiring TGA and DSC data. This work was funded by Solvay S.A., the Office of Naval Research , and the STC Program of the National Science Foundation ( DMR-0120967 ).

PY - 2012/2/28

Y1 - 2012/2/28

N2 - A series of conjugated polymers has been synthesized by Sonogashira coupling of N,N′-bis(2-octyldodecyl)-2,6-dibromonaphthalene-1,4,5,8- bis(dicarboximide) and four para-diethynylbenzene derivatives: 1,4-diethynyl-2,5-dihexadecyloxybenzene, 1,4-diethynyl-2,5-bis(2- octyldodecyloxy) benzene, 1,4-bis(2-ethylhexyl)-2,5-diethynylbenzene, 1,4-diethynyl-2,5-bis(trifluoromethyl)benzene. The polymers display absorption maxima at wavelengths ranging from 530 nm to 654 nm with molar absorptivities ranging from ca. 4 to 7 × 104 M-1 cm-1. The peak reduction potentials, determined by differential pulse voltammetry, for polymer films varied from -0.93 to -1.14 V vs. ferrocenium/ferrocene with the trifluoromethyl-substituted derivative being the most readily reduced. All four polymers exhibited electron transport characteristics in bottom-gate/top-contact field-effect transistors, showing average electron mobility values ranging from 1.4 × 10-4 to 3.7 × 10-3 cm2 V-1 s-1.

AB - A series of conjugated polymers has been synthesized by Sonogashira coupling of N,N′-bis(2-octyldodecyl)-2,6-dibromonaphthalene-1,4,5,8- bis(dicarboximide) and four para-diethynylbenzene derivatives: 1,4-diethynyl-2,5-dihexadecyloxybenzene, 1,4-diethynyl-2,5-bis(2- octyldodecyloxy) benzene, 1,4-bis(2-ethylhexyl)-2,5-diethynylbenzene, 1,4-diethynyl-2,5-bis(trifluoromethyl)benzene. The polymers display absorption maxima at wavelengths ranging from 530 nm to 654 nm with molar absorptivities ranging from ca. 4 to 7 × 104 M-1 cm-1. The peak reduction potentials, determined by differential pulse voltammetry, for polymer films varied from -0.93 to -1.14 V vs. ferrocenium/ferrocene with the trifluoromethyl-substituted derivative being the most readily reduced. All four polymers exhibited electron transport characteristics in bottom-gate/top-contact field-effect transistors, showing average electron mobility values ranging from 1.4 × 10-4 to 3.7 × 10-3 cm2 V-1 s-1.

KW - Conjugated polymers

KW - Electron transport

KW - Naphthalene diimide polymers

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DO - 10.1016/j.polymer.2012.01.016

M3 - Article

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SN - 0032-3861

VL - 53

SP - 1072

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JO - Polymer

JF - Polymer

IS - 5

ER -

Synthesis and characterization of naphthalene diimide/diethynylbenzene copolymers

Abstract

Bibliographical note

Keywords

ASJC Scopus subject areas

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