Stepwise cyanation of naphthalene diimide for n-channel field-effect transistors

Jingjing Chang; Qun Ye; Kuo-Wei Huang; Jie Zhang; Zhikuan Chen; Jishan Wu; Chunyan Chi

doi:10.1021/ol300914k

Stepwise cyanation of naphthalene diimide for n-channel field-effect transistors

Jingjing Chang, Qun Ye, Kuo-Wei Huang, Jie Zhang, Zhikuan Chen, Jishan Wu, Chunyan Chi

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

89 Scopus citations

Abstract

Stepwise cyanation of tetrabromonaphthalenediimide (NDI) 1 gave a series of cyanated NDIs 2-5 with the monocyanated NDI 2 and dicyanated NDI 3 isolated. The tri- and tetracyano- NDIs 4 and 5 show intrinsic instability toward moisture because of their extremely low-lying LUMO energy levels. The partially cyanated intermediates can be utilized as air-stable n-type semiconductors with OFET electron mobility up to 0.05 cm 2 V -1 s -1. © 2012 American Chemical Society.

Original language	English (US)
Pages (from-to)	2964-2967
Number of pages	4
Journal	Organic Letters
Volume	14
Issue number	12
DOIs	https://doi.org/10.1021/ol300914k
State	Published - May 25 2012

ASJC Scopus subject areas

Biochemistry
Organic Chemistry
Physical and Theoretical Chemistry

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10.1021/ol300914k

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@article{675101568a1c4176970e7661099bd347,

title = "Stepwise cyanation of naphthalene diimide for n-channel field-effect transistors",

abstract = "Stepwise cyanation of tetrabromonaphthalenediimide (NDI) 1 gave a series of cyanated NDIs 2-5 with the monocyanated NDI 2 and dicyanated NDI 3 isolated. The tri- and tetracyano- NDIs 4 and 5 show intrinsic instability toward moisture because of their extremely low-lying LUMO energy levels. The partially cyanated intermediates can be utilized as air-stable n-type semiconductors with OFET electron mobility up to 0.05 cm 2 V -1 s -1. {\textcopyright} 2012 American Chemical Society.",

author = "Jingjing Chang and Qun Ye and Kuo-Wei Huang and Jie Zhang and Zhikuan Chen and Jishan Wu and Chunyan Chi",

note = "KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: C.C. acknowledges financial support from the National University of Singapore start-up grant R-143-000-486-133 and MOE AcRF FRC grant R-143-000-444-112. K.-W.H. acknowledges financial support from KAUST. We thank Dr. Tan Geok Kheng at NUS for crystallographic analysis.",

year = "2012",

month = may,

day = "25",

doi = "10.1021/ol300914k",

language = "English (US)",

volume = "14",

pages = "2964--2967",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

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TY - JOUR

T1 - Stepwise cyanation of naphthalene diimide for n-channel field-effect transistors

AU - Chang, Jingjing

AU - Ye, Qun

AU - Huang, Kuo-Wei

AU - Zhang, Jie

AU - Chen, Zhikuan

AU - Wu, Jishan

AU - Chi, Chunyan

N1 - KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: C.C. acknowledges financial support from the National University of Singapore start-up grant R-143-000-486-133 and MOE AcRF FRC grant R-143-000-444-112. K.-W.H. acknowledges financial support from KAUST. We thank Dr. Tan Geok Kheng at NUS for crystallographic analysis.

PY - 2012/5/25

Y1 - 2012/5/25

N2 - Stepwise cyanation of tetrabromonaphthalenediimide (NDI) 1 gave a series of cyanated NDIs 2-5 with the monocyanated NDI 2 and dicyanated NDI 3 isolated. The tri- and tetracyano- NDIs 4 and 5 show intrinsic instability toward moisture because of their extremely low-lying LUMO energy levels. The partially cyanated intermediates can be utilized as air-stable n-type semiconductors with OFET electron mobility up to 0.05 cm 2 V -1 s -1. © 2012 American Chemical Society.

AB - Stepwise cyanation of tetrabromonaphthalenediimide (NDI) 1 gave a series of cyanated NDIs 2-5 with the monocyanated NDI 2 and dicyanated NDI 3 isolated. The tri- and tetracyano- NDIs 4 and 5 show intrinsic instability toward moisture because of their extremely low-lying LUMO energy levels. The partially cyanated intermediates can be utilized as air-stable n-type semiconductors with OFET electron mobility up to 0.05 cm 2 V -1 s -1. © 2012 American Chemical Society.

UR - http://hdl.handle.net/10754/562220

UR - https://pubs.acs.org/doi/10.1021/ol300914k

UR - http://www.scopus.com/inward/record.url?scp=84862576946&partnerID=8YFLogxK

U2 - 10.1021/ol300914k

DO - 10.1021/ol300914k

M3 - Article

SN - 1523-7060

VL - 14

SP - 2964

EP - 2967

JO - Organic Letters

JF - Organic Letters

IS - 12

ER -

Stepwise cyanation of naphthalene diimide for n-channel field-effect transistors

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CCDC 893180: Experimental Crystal Structure Determination : 5,10-bis((4-t-butylphenyl)sulfanyl)-2,7-dioctyl-1,3,6,8-tetraoxo-1,2,3,6,7,8-hexahydrobenzo[lmn][3,8]phenanthroline-4,9-dicarbonitrile chloroform solvate

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Stepwise cyanation of naphthalene diimide for n-channel field-effect transistors

Abstract

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CCDC 893180: Experimental Crystal Structure Determination : 5,10-bis((4-t-butylphenyl)sulfanyl)-2,7-dioctyl-1,3,6,8-tetraoxo-1,2,3,6,7,8-hexahydrobenzo[lmn][3,8]phenanthroline-4,9-dicarbonitrile chloroform solvate

Cite this