Stable 7,14-disubstituted-5,12-dithiapentacenes with quinoidal conjugation

Qun Ye; Jingjing Chang; Xueliang Shi; Gaole Dai; Wenhua Zhang; Kuo-Wei Huang; Chunyan Chi

doi:10.1021/ol5017756

Stable 7,14-disubstituted-5,12-dithiapentacenes with quinoidal conjugation

Qun Ye, Jingjing Chang, Xueliang Shi, Gaole Dai, Wenhua Zhang, Kuo-Wei Huang, Chunyan Chi

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

40 Scopus citations

Abstract

Two 7,14-disubstituted-5,12-dithiapentacenes (1 and 2) with quinoidal conjugation were synthesized. Their ground-state quinoidal structures were proven by X-ray crystallographic analysis. They showed very different electronic and optical properties from those of the corresponding pentacene derivatives with diene conjugation, and their stability was significantly improved. Organic field effect transistors based on solution processed thin films of 1 and 2 exhibited a hole mobility of up to 0.032 cm-2 V-1 s -1. © 2014 American Chemical Society.

Original language	English (US)
Pages (from-to)	3966-3969
Number of pages	4
Journal	Organic Letters
Volume	16
Issue number	15
DOIs	https://doi.org/10.1021/ol5017756
State	Published - Jul 14 2014

ASJC Scopus subject areas

Biochemistry
Organic Chemistry
Physical and Theoretical Chemistry

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10.1021/ol5017756

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@article{4ac4668096bb4f628f8d23e545647fe8,

title = "Stable 7,14-disubstituted-5,12-dithiapentacenes with quinoidal conjugation",

abstract = "Two 7,14-disubstituted-5,12-dithiapentacenes (1 and 2) with quinoidal conjugation were synthesized. Their ground-state quinoidal structures were proven by X-ray crystallographic analysis. They showed very different electronic and optical properties from those of the corresponding pentacene derivatives with diene conjugation, and their stability was significantly improved. Organic field effect transistors based on solution processed thin films of 1 and 2 exhibited a hole mobility of up to 0.032 cm-2 V-1 s -1. {\textcopyright} 2014 American Chemical Society.",

author = "Qun Ye and Jingjing Chang and Xueliang Shi and Gaole Dai and Wenhua Zhang and Kuo-Wei Huang and Chunyan Chi",

note = "KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: C.C. acknowledges financial support from the NUS Start-Up grant (R-143-000-486-133) and MOE AcRF Tier 1 grants (R-143-000-510-112 and R-143-000-573-112). K.H. acknowledges financial support from KAUST.",

year = "2014",

month = jul,

day = "14",

doi = "10.1021/ol5017756",

language = "English (US)",

volume = "16",

pages = "3966--3969",

journal = "Organic Letters",

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TY - JOUR

T1 - Stable 7,14-disubstituted-5,12-dithiapentacenes with quinoidal conjugation

AU - Ye, Qun

AU - Chang, Jingjing

AU - Shi, Xueliang

AU - Dai, Gaole

AU - Zhang, Wenhua

AU - Huang, Kuo-Wei

AU - Chi, Chunyan

N1 - KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: C.C. acknowledges financial support from the NUS Start-Up grant (R-143-000-486-133) and MOE AcRF Tier 1 grants (R-143-000-510-112 and R-143-000-573-112). K.H. acknowledges financial support from KAUST.

PY - 2014/7/14

Y1 - 2014/7/14

N2 - Two 7,14-disubstituted-5,12-dithiapentacenes (1 and 2) with quinoidal conjugation were synthesized. Their ground-state quinoidal structures were proven by X-ray crystallographic analysis. They showed very different electronic and optical properties from those of the corresponding pentacene derivatives with diene conjugation, and their stability was significantly improved. Organic field effect transistors based on solution processed thin films of 1 and 2 exhibited a hole mobility of up to 0.032 cm-2 V-1 s -1. © 2014 American Chemical Society.

AB - Two 7,14-disubstituted-5,12-dithiapentacenes (1 and 2) with quinoidal conjugation were synthesized. Their ground-state quinoidal structures were proven by X-ray crystallographic analysis. They showed very different electronic and optical properties from those of the corresponding pentacene derivatives with diene conjugation, and their stability was significantly improved. Organic field effect transistors based on solution processed thin films of 1 and 2 exhibited a hole mobility of up to 0.032 cm-2 V-1 s -1. © 2014 American Chemical Society.

UR - http://hdl.handle.net/10754/563682

UR - https://pubs.acs.org/doi/10.1021/ol5017756

UR - http://www.scopus.com/inward/record.url?scp=84905407396&partnerID=8YFLogxK

U2 - 10.1021/ol5017756

DO - 10.1021/ol5017756

M3 - Article

SN - 1523-7060

VL - 16

SP - 3966

EP - 3969

JO - Organic Letters

JF - Organic Letters

IS - 15

ER -

Stable 7,14-disubstituted-5,12-dithiapentacenes with quinoidal conjugation

Abstract

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CCDC 1817905: Experimental Crystal Structure Determination : [(2,9-di-t-butyl[1]benzothiopyrano[2,3-b]thioxanthene-7,14-diyl)bis(ethyne-2,1-diyl)]bis[triisopropylsilane]

CCDC 1817904: Experimental Crystal Structure Determination : 2,9-di-t-butyl-7,14-diphenyl[1]benzothiopyrano[2,3-b]thioxanthene

Cite this

Stable 7,14-disubstituted-5,12-dithiapentacenes with quinoidal conjugation

Abstract

ASJC Scopus subject areas

Access to Document

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Datasets

CCDC 1817905: Experimental Crystal Structure Determination : [(2,9-di-t-butyl[1]benzothiopyrano[2,3-b]thioxanthene-7,14-diyl)bis(ethyne-2,1-diyl)]bis[triisopropylsilane]

CCDC 1817904: Experimental Crystal Structure Determination : 2,9-di-t-butyl-7,14-diphenyl[1]benzothiopyrano[2,3-b]thioxanthene

Cite this