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

68 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
General Chemistry
Catalysis
Electronic, Optical and Magnetic Materials

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10.1039/c4cc07630c

Cite this

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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.).",

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doi = "10.1039/c4cc07630c",

language = "English (US)",

volume = "51",

pages = "503--506",

journal = "Chem. Commun.",

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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

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EP - 506

JO - Chem. Commun.

JF - Chem. Commun.

IS - 3

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

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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

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

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

Abstract

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Datasets

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

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

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