Hexacene Diimides

Xiaoping Cui; Chengyi Xiao; Thorsten Winands; Tobias Koch; Yan Li; Lei Zhang; Nikos L. Doltsinis; Zhaohui Wang

doi:10.1021/jacs.8b07305

Hexacene Diimides

Xiaoping Cui
, Chengyi Xiao
, Thorsten Winands
, Tobias Koch
, Yan Li^*
, Lei Zhang
, Nikos L. Doltsinis
, Zhaohui Wang

^*Corresponding author for this work

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

63 Scopus citations

Abstract

Acene imides are expected to possess smaller band gaps than homologous acenes while maintaining good solubility and stability. However, the design and synthesis of large acene imides are still a big challenge. Herein, we report a one-pot synthesis of hexacene diimides (HDI) by double aromatic annulation between zirconabenzocyclopentene and tetrabrominated naphthalene diimides. HDIs with branched alkyl chains exhibit very good solubility, stability, and much smaller band gaps than hexacene. Organic field-effect transistors (OFETs) based on HDI microribbons exhibit excellent ambipolar transport behavior with the highest electron mobility of 2.17 cm² V^-1 s^-1 and hole mobility of 0.30 cm² V^-1 s^-1 under ambient conditions.

Original language	English
Pages (from-to)	12175-12180
Number of pages	6
Journal	Journal of the American Chemical Society
Volume	140
Issue number	38
DOIs	https://doi.org/10.1021/jacs.8b07305
State	Published - 26 Sep 2018
Externally published	Yes

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title = "Hexacene Diimides",

abstract = "Acene imides are expected to possess smaller band gaps than homologous acenes while maintaining good solubility and stability. However, the design and synthesis of large acene imides are still a big challenge. Herein, we report a one-pot synthesis of hexacene diimides (HDI) by double aromatic annulation between zirconabenzocyclopentene and tetrabrominated naphthalene diimides. HDIs with branched alkyl chains exhibit very good solubility, stability, and much smaller band gaps than hexacene. Organic field-effect transistors (OFETs) based on HDI microribbons exhibit excellent ambipolar transport behavior with the highest electron mobility of 2.17 cm2 V-1 s-1 and hole mobility of 0.30 cm2 V-1 s-1 under ambient conditions.",

author = "Xiaoping Cui and Chengyi Xiao and Thorsten Winands and Tobias Koch and Yan Li and Lei Zhang and Doltsinis, \{Nikos L.\} and Zhaohui Wang",

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doi = "10.1021/jacs.8b07305",

language = "英语",

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TY - JOUR

T1 - Hexacene Diimides

AU - Cui, Xiaoping

AU - Xiao, Chengyi

AU - Winands, Thorsten

AU - Koch, Tobias

AU - Li, Yan

AU - Zhang, Lei

AU - Doltsinis, Nikos L.

AU - Wang, Zhaohui

PY - 2018/9/26

Y1 - 2018/9/26

N2 - Acene imides are expected to possess smaller band gaps than homologous acenes while maintaining good solubility and stability. However, the design and synthesis of large acene imides are still a big challenge. Herein, we report a one-pot synthesis of hexacene diimides (HDI) by double aromatic annulation between zirconabenzocyclopentene and tetrabrominated naphthalene diimides. HDIs with branched alkyl chains exhibit very good solubility, stability, and much smaller band gaps than hexacene. Organic field-effect transistors (OFETs) based on HDI microribbons exhibit excellent ambipolar transport behavior with the highest electron mobility of 2.17 cm2 V-1 s-1 and hole mobility of 0.30 cm2 V-1 s-1 under ambient conditions.

AB - Acene imides are expected to possess smaller band gaps than homologous acenes while maintaining good solubility and stability. However, the design and synthesis of large acene imides are still a big challenge. Herein, we report a one-pot synthesis of hexacene diimides (HDI) by double aromatic annulation between zirconabenzocyclopentene and tetrabrominated naphthalene diimides. HDIs with branched alkyl chains exhibit very good solubility, stability, and much smaller band gaps than hexacene. Organic field-effect transistors (OFETs) based on HDI microribbons exhibit excellent ambipolar transport behavior with the highest electron mobility of 2.17 cm2 V-1 s-1 and hole mobility of 0.30 cm2 V-1 s-1 under ambient conditions.

UR - https://www.scopus.com/pages/publications/85052989631

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DO - 10.1021/jacs.8b07305

M3 - 文章

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JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 38

ER -

Hexacene Diimides

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