Conjugated Copolymers of Vinylene Flanked Naphthalene Diimide

Zhuping Fei; Yang Han; Jaime Martin; Fiona H. Scholes; Mohammed Al-Hashimi; Siham Y. Alqaradawi; Natalie Stingelin; Thomas D. Anthopoulos; Martin Heeney

doi:10.1021/acs.macromol.6b01423

Conjugated Copolymers of Vinylene Flanked Naphthalene Diimide

Zhuping Fei, Yang Han, Jaime Martin, Fiona H. Scholes, Mohammed Al-Hashimi, Siham Y. Alqaradawi, Natalie Stingelin, Thomas D. Anthopoulos, Martin Heeney

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

50 Scopus citations

Abstract

We report the synthesis of a novel naphthalene diimide (NDI) monomer containing two (tributylstannyl)vinyl groups. The utility of this building block is demonstrated by its copolymerization with five different electron-rich comonomers under Stille conditions. The resulting high molecular weight polymers show red-shifted optical absorptions in comparison to the analogous polymers without the vinylene spacer and a significant increase in the intensity of the low-energy intramolecular charge transfer band. The polymers all exhibit ambipolar behavior in bottom-gate, top-contact organic thin-film transistors. The insertion of a solution-processed barium hydroxide layer between the polymer and the gold electrode led to unipolar behavior with improved electron mobilities.

Original language	English (US)
Pages (from-to)	6384-6393
Number of pages	10
Journal	Macromolecules
Volume	49
Issue number	17
DOIs	https://doi.org/10.1021/acs.macromol.6b01423
State	Published - Sep 13 2016
Externally published	Yes

Bibliographical note

Generated from Scopus record by KAUST IRTS on 2023-02-14

ASJC Scopus subject areas

Materials Chemistry
Organic Chemistry
Polymers and Plastics
Inorganic Chemistry

Access to Document

10.1021/acs.macromol.6b01423

Cite this

@article{06e235e92f404963a7160e69a2901b20,

title = "Conjugated Copolymers of Vinylene Flanked Naphthalene Diimide",

abstract = "We report the synthesis of a novel naphthalene diimide (NDI) monomer containing two (tributylstannyl)vinyl groups. The utility of this building block is demonstrated by its copolymerization with five different electron-rich comonomers under Stille conditions. The resulting high molecular weight polymers show red-shifted optical absorptions in comparison to the analogous polymers without the vinylene spacer and a significant increase in the intensity of the low-energy intramolecular charge transfer band. The polymers all exhibit ambipolar behavior in bottom-gate, top-contact organic thin-film transistors. The insertion of a solution-processed barium hydroxide layer between the polymer and the gold electrode led to unipolar behavior with improved electron mobilities.",

author = "Zhuping Fei and Yang Han and Jaime Martin and Scholes, {Fiona H.} and Mohammed Al-Hashimi and Alqaradawi, {Siham Y.} and Natalie Stingelin and Anthopoulos, {Thomas D.} and Martin Heeney",

note = "Generated from Scopus record by KAUST IRTS on 2023-02-14",

year = "2016",

month = sep,

day = "13",

doi = "10.1021/acs.macromol.6b01423",

language = "English (US)",

volume = "49",

pages = "6384--6393",

journal = "Macromolecules",

issn = "1520-5835",

publisher = "American Chemical Society",

number = "17",

}

TY - JOUR

T1 - Conjugated Copolymers of Vinylene Flanked Naphthalene Diimide

AU - Fei, Zhuping

AU - Han, Yang

AU - Martin, Jaime

AU - Scholes, Fiona H.

AU - Al-Hashimi, Mohammed

AU - Alqaradawi, Siham Y.

AU - Stingelin, Natalie

AU - Anthopoulos, Thomas D.

AU - Heeney, Martin

N1 - Generated from Scopus record by KAUST IRTS on 2023-02-14

PY - 2016/9/13

Y1 - 2016/9/13

N2 - We report the synthesis of a novel naphthalene diimide (NDI) monomer containing two (tributylstannyl)vinyl groups. The utility of this building block is demonstrated by its copolymerization with five different electron-rich comonomers under Stille conditions. The resulting high molecular weight polymers show red-shifted optical absorptions in comparison to the analogous polymers without the vinylene spacer and a significant increase in the intensity of the low-energy intramolecular charge transfer band. The polymers all exhibit ambipolar behavior in bottom-gate, top-contact organic thin-film transistors. The insertion of a solution-processed barium hydroxide layer between the polymer and the gold electrode led to unipolar behavior with improved electron mobilities.

AB - We report the synthesis of a novel naphthalene diimide (NDI) monomer containing two (tributylstannyl)vinyl groups. The utility of this building block is demonstrated by its copolymerization with five different electron-rich comonomers under Stille conditions. The resulting high molecular weight polymers show red-shifted optical absorptions in comparison to the analogous polymers without the vinylene spacer and a significant increase in the intensity of the low-energy intramolecular charge transfer band. The polymers all exhibit ambipolar behavior in bottom-gate, top-contact organic thin-film transistors. The insertion of a solution-processed barium hydroxide layer between the polymer and the gold electrode led to unipolar behavior with improved electron mobilities.

UR - https://pubs.acs.org/doi/10.1021/acs.macromol.6b01423

UR - http://www.scopus.com/inward/record.url?scp=84987644085&partnerID=8YFLogxK

U2 - 10.1021/acs.macromol.6b01423

DO - 10.1021/acs.macromol.6b01423

M3 - Article

SN - 1520-5835

VL - 49

SP - 6384

EP - 6393

JO - Macromolecules

JF - Macromolecules

IS - 17

ER -

Conjugated Copolymers of Vinylene Flanked Naphthalene Diimide

Abstract

Bibliographical note

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this