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

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

26 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
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

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 ).

Funding

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 ).

Funders	Funder number
Solvay S.A.
National Science Foundation Arctic Social Science Program	DMR-0120967
National Science Foundation Arctic Social Science Program
Office of Naval Research Naval Academy

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{28d6fb671f3e4aae934091452465eca5,

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",

month = feb,

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

language = "English",

volume = "53",

pages = "1072--1078",

number = "5",

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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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UR - https://www.scopus.com/pages/publications/84862777751#tab=citedBy

U2 - 10.1016/j.polymer.2012.01.016

DO - 10.1016/j.polymer.2012.01.016

M3 - Article

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SN - 0032-3861

VL - 53

SP - 1072

EP - 1078

JO - Polymer

JF - Polymer

IS - 5

ER -

Synthesis and characterization of naphthalene diimide/diethynylbenzene copolymers

Abstract

Bibliographical note

Funding

Keywords

ASJC Scopus subject areas

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