Dianthraceno[a,e]pentalenes: Synthesis, crystallographic structures and applications in organic field-effect transistors

Gaole Dai; Jingjing Chang; Wenhua Zhang; Shiqiang Bai; Kuo-Wei Huang; Jianwei Xu; Chunyan Chi

doi:10.1039/c4cc07630c

Dianthraceno[a,e]pentalenes: Synthesis, crystallographic structures and applications in organic field-effect transistors

Gaole Dai, Jingjing Chang, Wenhua Zhang, Shiqiang Bai, Kuo-Wei Huang, Jianwei Xu, Chunyan Chi

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

47 Scopus citations

Abstract

Two soluble and stable dianthraceno[a,e]pentalenes with two (DAP1) and six (DAP2) phenyl substituents were synthesized. Both compounds possess a small energy band gap and show amphoteric redox behaviour due to intramolecular donor-accepter interactions. X-ray crystallographic analysis revealed that DAP2 has a closely packed structure with multi-dimensional [C-H⋯π] interactions although there are no π-π interactions between the dianthraceno[a,e]pentalene cores. As a result, solution-processed field effect transistors based on DAP2 exhibited an average hole mobility of 0.65 cm2 V-1 s-1. Under similar conditions, DAP1 showed an average field effect hole mobility of 0.001 cm2 V-1 s-1. This journal is

Original language	English (US)
Pages (from-to)	503-506
Number of pages	4
Journal	Chem. Commun.
Volume	51
Issue number	3
DOIs	https://doi.org/10.1039/c4cc07630c
State	Published - 2015

ASJC Scopus subject areas

Materials Chemistry
Surfaces, Coatings and Films
Metals and Alloys
Ceramics and Composites
Chemistry(all)
Catalysis
Electronic, Optical and Magnetic Materials

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10.1039/c4cc07630c

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CCDC 1008483: Experimental Crystal Structure Determination : 7,16-bis(4-nonylphenyl)anthra[2',3':4,5]pentaleno[1,2-b]anthracene
Dai, G. (Creator), Chang, J. (Creator), Zhang, W. (Creator), Bai, S. (Creator), Huang, K. (Creator), Xu, J. (Creator), Chi, C. (Creator), Dai, G. (Creator), Chang, J. (Creator), Zhang, W. (Creator), Bai, S. (Creator), Xu, J. (Creator) & Chi, C. (Creator), Cambridge Crystallographic Data Centre, Nov 19 2014
DOI: 10.5517/cc12vdq1, http://hdl.handle.net/10754/624337
Dataset
CCDC 1008484: Experimental Crystal Structure Determination : 7,16-bis(4-nonylphenyl)-5,9,14,18-tetraphenylanthra[2',3':4,5]pentaleno[1,2-b]anthracene unknown solvate
Dai, G. (Creator), Chang, J. (Creator), Zhang, W. (Creator), Bai, S. (Creator), Huang, K. (Creator), Xu, J. (Creator), Chi, C. (Creator), Dai, G. (Creator), Chang, J. (Creator), Zhang, W. (Creator), Bai, S. (Creator), Xu, J. (Creator) & Chi, C. (Creator), Cambridge Crystallographic Data Centre, Nov 19 2014
DOI: 10.5517/cc12vdr2, http://hdl.handle.net/10754/624338
Dataset

Cite this

@article{4e09fddaafbd4ebaa13901dc0b06da2b,

title = "Dianthraceno[a,e]pentalenes: Synthesis, crystallographic structures and applications in organic field-effect transistors",

abstract = "Two soluble and stable dianthraceno[a,e]pentalenes with two (DAP1) and six (DAP2) phenyl substituents were synthesized. Both compounds possess a small energy band gap and show amphoteric redox behaviour due to intramolecular donor-accepter interactions. X-ray crystallographic analysis revealed that DAP2 has a closely packed structure with multi-dimensional [C-H⋯π] interactions although there are no π-π interactions between the dianthraceno[a,e]pentalene cores. As a result, solution-processed field effect transistors based on DAP2 exhibited an average hole mobility of 0.65 cm2 V-1 s-1. Under similar conditions, DAP1 showed an average field effect hole mobility of 0.001 cm2 V-1 s-1. This journal is",

author = "Gaole Dai and Jingjing Chang and Wenhua Zhang and Shiqiang Bai and Kuo-Wei Huang and Jianwei Xu and Chunyan Chi",

note = "KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: This work was financially supported by the NUS Start-Up Grant (R-143-000-486-133) and MOE AcRF grants (R-143-000510-112 and R-143-000-573-112) (C. C.), the NUS-IMRE Molecular Material Center (J. X.), and KAUST (K. W. H.).",

year = "2015",

doi = "10.1039/c4cc07630c",

language = "English (US)",

volume = "51",

pages = "503--506",

journal = "Chem. Commun.",

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publisher = "Royal Society of Chemistry",

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T1 - Dianthraceno[a,e]pentalenes: Synthesis, crystallographic structures and applications in organic field-effect transistors

AU - Dai, Gaole

AU - Chang, Jingjing

AU - Zhang, Wenhua

AU - Bai, Shiqiang

AU - Huang, Kuo-Wei

AU - Xu, Jianwei

AU - Chi, Chunyan

N1 - KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: This work was financially supported by the NUS Start-Up Grant (R-143-000-486-133) and MOE AcRF grants (R-143-000510-112 and R-143-000-573-112) (C. C.), the NUS-IMRE Molecular Material Center (J. X.), and KAUST (K. W. H.).

PY - 2015

Y1 - 2015

N2 - Two soluble and stable dianthraceno[a,e]pentalenes with two (DAP1) and six (DAP2) phenyl substituents were synthesized. Both compounds possess a small energy band gap and show amphoteric redox behaviour due to intramolecular donor-accepter interactions. X-ray crystallographic analysis revealed that DAP2 has a closely packed structure with multi-dimensional [C-H⋯π] interactions although there are no π-π interactions between the dianthraceno[a,e]pentalene cores. As a result, solution-processed field effect transistors based on DAP2 exhibited an average hole mobility of 0.65 cm2 V-1 s-1. Under similar conditions, DAP1 showed an average field effect hole mobility of 0.001 cm2 V-1 s-1. This journal is

AB - Two soluble and stable dianthraceno[a,e]pentalenes with two (DAP1) and six (DAP2) phenyl substituents were synthesized. Both compounds possess a small energy band gap and show amphoteric redox behaviour due to intramolecular donor-accepter interactions. X-ray crystallographic analysis revealed that DAP2 has a closely packed structure with multi-dimensional [C-H⋯π] interactions although there are no π-π interactions between the dianthraceno[a,e]pentalene cores. As a result, solution-processed field effect transistors based on DAP2 exhibited an average hole mobility of 0.65 cm2 V-1 s-1. Under similar conditions, DAP1 showed an average field effect hole mobility of 0.001 cm2 V-1 s-1. This journal is

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DO - 10.1039/c4cc07630c

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SN - 1359-7345

IS - 3

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Dianthraceno[a,e]pentalenes: Synthesis, crystallographic structures and applications in organic field-effect transistors

Abstract

ASJC Scopus subject areas

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CCDC 1008483: Experimental Crystal Structure Determination : 7,16-bis(4-nonylphenyl)anthra[2',3':4,5]pentaleno[1,2-b]anthracene

CCDC 1008484: Experimental Crystal Structure Determination : 7,16-bis(4-nonylphenyl)-5,9,14,18-tetraphenylanthra[2',3':4,5]pentaleno[1,2-b]anthracene unknown solvate

Cite this