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

Bibliographical 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.

ASJC Scopus subject areas

Biochemistry
Organic Chemistry
Physical and Theoretical Chemistry

Access to Document

10.1021/ol300914k

Cite this

@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",

number = "12",

}

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

Abstract

Bibliographical note

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

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

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

Abstract

Bibliographical note

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Datasets

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