Dipolar Quinoidal Acene Analogues as Stable Isoelectronic Structures of Pentacene and Nonacene

Xueliang Shi; Weixiang Kueh; Bin Zheng; Kuo-Wei Huang; Chunyan Chi

doi:10.1002/anie.201507573

Dipolar Quinoidal Acene Analogues as Stable Isoelectronic Structures of Pentacene and Nonacene

Xueliang Shi, Weixiang Kueh, Bin Zheng, Kuo-Wei Huang, Chunyan Chi

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39 Scopus citations

Abstract

Quinoidal thia-acene analogues, as the respective isoelectronic structures of pentacene and nonacene, were synthesized and an unusual 1,2-sulfur migration was observed during the Friedel-Crafts alkylation reaction. The analogues display a closed-shell quinoidal structure in the ground state with a distinctive dipolar character. In contrast to their acene isoelectronic structures, both compounds are stable because of the existence of more aromatic sextet rings, a dipolar character, and kinetic blocking. They exhibit unique packing in single crystals resulting from balanced dipole-dipole and [C-H⋯π]/[C-H⋯S] interactions.

Original language	English (US)
Pages (from-to)	14412-14416
Number of pages	5
Journal	Angewandte Chemie International Edition
Volume	54
Issue number	48
DOIs	https://doi.org/10.1002/anie.201507573 https://doi.org/10.1002/ange.201507573
State	Published - Oct 8 2015

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@article{50654acfbd3643f3bf697daf2dac39c2,

title = "Dipolar Quinoidal Acene Analogues as Stable Isoelectronic Structures of Pentacene and Nonacene",

abstract = "Quinoidal thia-acene analogues, as the respective isoelectronic structures of pentacene and nonacene, were synthesized and an unusual 1,2-sulfur migration was observed during the Friedel-Crafts alkylation reaction. The analogues display a closed-shell quinoidal structure in the ground state with a distinctive dipolar character. In contrast to their acene isoelectronic structures, both compounds are stable because of the existence of more aromatic sextet rings, a dipolar character, and kinetic blocking. They exhibit unique packing in single crystals resulting from balanced dipole-dipole and [C-H⋯π]/[C-H⋯S] interactions.",

author = "Xueliang Shi and Weixiang Kueh and Bin Zheng and Kuo-Wei Huang and Chunyan Chi",

note = "KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: C.C. acknowledges financial support from the MOE Tier 1 grant (R-143-000-573-112), Tier 2 grant (MOE2014-T2-1-080), and Tier 3 programme (MOE2014-T3-1-004). K.-W.H. acknowledges financial support from KAUST. We thank Dr. Bruno Donnadieu and Dr. Tan Geok Kheng for the crystallographic analysis.",

year = "2015",

month = oct,

day = "8",

doi = "10.1002/anie.201507573",

language = "English (US)",

volume = "54",

pages = "14412--14416",

journal = "Angewandte Chemie International Edition",

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T1 - Dipolar Quinoidal Acene Analogues as Stable Isoelectronic Structures of Pentacene and Nonacene

AU - Shi, Xueliang

AU - Kueh, Weixiang

AU - Zheng, Bin

AU - Huang, Kuo-Wei

AU - Chi, Chunyan

N1 - KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: C.C. acknowledges financial support from the MOE Tier 1 grant (R-143-000-573-112), Tier 2 grant (MOE2014-T2-1-080), and Tier 3 programme (MOE2014-T3-1-004). K.-W.H. acknowledges financial support from KAUST. We thank Dr. Bruno Donnadieu and Dr. Tan Geok Kheng for the crystallographic analysis.

PY - 2015/10/8

Y1 - 2015/10/8

N2 - Quinoidal thia-acene analogues, as the respective isoelectronic structures of pentacene and nonacene, were synthesized and an unusual 1,2-sulfur migration was observed during the Friedel-Crafts alkylation reaction. The analogues display a closed-shell quinoidal structure in the ground state with a distinctive dipolar character. In contrast to their acene isoelectronic structures, both compounds are stable because of the existence of more aromatic sextet rings, a dipolar character, and kinetic blocking. They exhibit unique packing in single crystals resulting from balanced dipole-dipole and [C-H⋯π]/[C-H⋯S] interactions.

AB - Quinoidal thia-acene analogues, as the respective isoelectronic structures of pentacene and nonacene, were synthesized and an unusual 1,2-sulfur migration was observed during the Friedel-Crafts alkylation reaction. The analogues display a closed-shell quinoidal structure in the ground state with a distinctive dipolar character. In contrast to their acene isoelectronic structures, both compounds are stable because of the existence of more aromatic sextet rings, a dipolar character, and kinetic blocking. They exhibit unique packing in single crystals resulting from balanced dipole-dipole and [C-H⋯π]/[C-H⋯S] interactions.

UR - http://hdl.handle.net/10754/623136

UR - http://doi.wiley.com/10.1002/anie.201507573

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DO - 10.1002/anie.201507573

M3 - Article

C2 - 26447720

SN - 1433-7851

VL - 54

SP - 14412

EP - 14416

JO - Angewandte Chemie International Edition

JF - Angewandte Chemie International Edition

IS - 48

ER -

Dipolar Quinoidal Acene Analogues as Stable Isoelectronic Structures of Pentacene and Nonacene

Abstract

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CCDC 1408042: Experimental Crystal Structure Determination : 6,13-dimesitylpentacene

CCDC 1059906: Experimental Crystal Structure Determination : 5,11,17,19-tetramesitylindeno[1,2-b]indeno[1',2':6,7]thiochromeno[2,3-i]thioxanthene toluene solvate

CCDC 1059907: Experimental Crystal Structure Determination : (1,4-phenylenebis(sulfanediylbiphenyl-4,2,5-triyl))tetrakis(mesitylmethanone)

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Dipolar Quinoidal Acene Analogues as Stable Isoelectronic Structures of Pentacene and Nonacene

Abstract

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Datasets

CCDC 1408042: Experimental Crystal Structure Determination : 6,13-dimesitylpentacene

CCDC 1059906: Experimental Crystal Structure Determination : 5,11,17,19-tetramesitylindeno[1,2-b]indeno[1',2':6,7]thiochromeno[2,3-i]thioxanthene toluene solvate

CCDC 1059907: Experimental Crystal Structure Determination : (1,4-phenylenebis(sulfanediylbiphenyl-4,2,5-triyl))tetrakis(mesitylmethanone)

Cite this