TCNQ-embedded heptacene and nonacene: Synthesis, characterization and physical properties

Qun Ye; Jingjing Chang; Kuo-Wei Huang; Gaole Dai; Chunyan Chi

doi:10.1039/c3ob40796a

TCNQ-embedded heptacene and nonacene: Synthesis, characterization and physical properties

Qun Ye, Jingjing Chang, Kuo-Wei Huang, Gaole Dai, Chunyan Chi

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Abstract

Incorporation of 7,7,8,8-tetracyanoquinodimethane (TCNQ) moieties into the acene backbone has been successfully achieved and two heptacene-TCNQ derivatives and one nonacene-TCNQ derivative have been synthesized and well characterized. Two TCNQ moieties have been embedded into heptacene and nonacene backbones for the first time. All the three compounds have good stability and solubility due to the presence of TCNQ moieties. Single crystal analysis revealed a bent butterfly-like conformation of these molecules. Their charge transport properties have been characterized using organic field effect transistors (OFETs). © 2013 The Royal Society of Chemistry.

Original language	English (US)
Pages (from-to)	6285
Journal	Organic and Biomolecular Chemistry
Volume	11
Issue number	37
DOIs	https://doi.org/10.1039/c3ob40796a
State	Published - 2013

ASJC Scopus subject areas

Biochemistry
Organic Chemistry
Physical and Theoretical Chemistry

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10.1039/c3ob40796a

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title = "TCNQ-embedded heptacene and nonacene: Synthesis, characterization and physical properties",

abstract = "Incorporation of 7,7,8,8-tetracyanoquinodimethane (TCNQ) moieties into the acene backbone has been successfully achieved and two heptacene-TCNQ derivatives and one nonacene-TCNQ derivative have been synthesized and well characterized. Two TCNQ moieties have been embedded into heptacene and nonacene backbones for the first time. All the three compounds have good stability and solubility due to the presence of TCNQ moieties. Single crystal analysis revealed a bent butterfly-like conformation of these molecules. Their charge transport properties have been characterized using organic field effect transistors (OFETs). {\textcopyright} 2013 The Royal Society of Chemistry.",

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

note = "KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: This work was financially supported by Singapore MOE AcRF grant R-143-000-510-112 (C. C.), NUS Start Up grant R-143-000-486-133 (C. C.) and KAUST (K.-W. H.). We thank Mdm. Tan Geok Kheng for the crystallographic analysis.",

year = "2013",

doi = "10.1039/c3ob40796a",

language = "English (US)",

volume = "11",

pages = "6285",

journal = "Organic and Biomolecular Chemistry",

issn = "1477-0520",

publisher = "Royal Society of Chemistry",

number = "37",

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TY - JOUR

T1 - TCNQ-embedded heptacene and nonacene: Synthesis, characterization and physical properties

AU - Ye, Qun

AU - Chang, Jingjing

AU - Huang, Kuo-Wei

AU - Dai, Gaole

AU - Chi, Chunyan

N1 - KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: This work was financially supported by Singapore MOE AcRF grant R-143-000-510-112 (C. C.), NUS Start Up grant R-143-000-486-133 (C. C.) and KAUST (K.-W. H.). We thank Mdm. Tan Geok Kheng for the crystallographic analysis.

PY - 2013

Y1 - 2013

N2 - Incorporation of 7,7,8,8-tetracyanoquinodimethane (TCNQ) moieties into the acene backbone has been successfully achieved and two heptacene-TCNQ derivatives and one nonacene-TCNQ derivative have been synthesized and well characterized. Two TCNQ moieties have been embedded into heptacene and nonacene backbones for the first time. All the three compounds have good stability and solubility due to the presence of TCNQ moieties. Single crystal analysis revealed a bent butterfly-like conformation of these molecules. Their charge transport properties have been characterized using organic field effect transistors (OFETs). © 2013 The Royal Society of Chemistry.

AB - Incorporation of 7,7,8,8-tetracyanoquinodimethane (TCNQ) moieties into the acene backbone has been successfully achieved and two heptacene-TCNQ derivatives and one nonacene-TCNQ derivative have been synthesized and well characterized. Two TCNQ moieties have been embedded into heptacene and nonacene backbones for the first time. All the three compounds have good stability and solubility due to the presence of TCNQ moieties. Single crystal analysis revealed a bent butterfly-like conformation of these molecules. Their charge transport properties have been characterized using organic field effect transistors (OFETs). © 2013 The Royal Society of Chemistry.

UR - http://hdl.handle.net/10754/562527

UR - http://xlink.rsc.org/?DOI=c3ob40796a

UR - http://www.scopus.com/inward/record.url?scp=84883428729&partnerID=8YFLogxK

U2 - 10.1039/c3ob40796a

DO - 10.1039/c3ob40796a

M3 - Article

SN - 1477-0520

VL - 11

SP - 6285

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

IS - 37

ER -

TCNQ-embedded heptacene and nonacene: Synthesis, characterization and physical properties

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CCDC 934853: Experimental Crystal Structure Determination : 2,2',2'',2'''-(7,16-bis((4-t-butylphenyl)sulfanyl)heptacene-5,9,14,18-tetraylidene)tetramalononitrile chloroform solvate

CCDC 934854: Experimental Crystal Structure Determination : 2,2'-(5,9,14,18-tetrakis(4-(trifluoromethyl)phenyl)heptacene-7,16-diylidene)dimalononitrile chloroform solvate

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TCNQ-embedded heptacene and nonacene: Synthesis, characterization and physical properties

Abstract

ASJC Scopus subject areas

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CCDC 934853: Experimental Crystal Structure Determination : 2,2',2'',2'''-(7,16-bis((4-t-butylphenyl)sulfanyl)heptacene-5,9,14,18-tetraylidene)tetramalononitrile chloroform solvate

CCDC 934854: Experimental Crystal Structure Determination : 2,2'-(5,9,14,18-tetrakis(4-(trifluoromethyl)phenyl)heptacene-7,16-diylidene)dimalononitrile chloroform solvate

Cite this