Bisindeno-annulated pentacenes with exceptionally high photo-stability and ordered molecular packing: Simple synthesis by a regio-selective Scholl reaction

Arun Naibi Lakshminarayana; Jingjing Chang; Jie Luo; Bin Zheng; Kuo-Wei Huang; Chunyan Chi

doi:10.1039/c4cc09812a

Bisindeno-annulated pentacenes with exceptionally high photo-stability and ordered molecular packing: Simple synthesis by a regio-selective Scholl reaction

Arun Naibi Lakshminarayana, Jingjing Chang, Jie Luo, Bin Zheng, Kuo-Wei Huang, Chunyan Chi

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

63 Scopus citations

Abstract

Bisindeno-annulated pentacenes 3a and 3b were synthesized by a simple regio-selective, FeCl3-mediated Scholl reaction from the corresponding 6,13-diaryl pentacene precursors. The fusion of two indeno-units dramatically changes the electronic properties and chemical reactivity of pentacene and the obtained compounds exhibited exceptionally high photo-stability in the solution, with a half-life time of 11.2 (3a) and 32.0 (3b) days under ambient light and air conditions. Ordered molecular packing with a small π-π stacking distance was observed in the single crystals of 3a and 3b. Our research provides a promising strategy to access stable higher order acenes with controlled molecular order. This journal is

Original language	English (US)
Pages (from-to)	3604-3607
Number of pages	4
Journal	Chem. Commun.
Volume	51
Issue number	17
DOIs	https://doi.org/10.1039/c4cc09812a
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/c4cc09812a

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title = "Bisindeno-annulated pentacenes with exceptionally high photo-stability and ordered molecular packing: Simple synthesis by a regio-selective Scholl reaction",

abstract = "Bisindeno-annulated pentacenes 3a and 3b were synthesized by a simple regio-selective, FeCl3-mediated Scholl reaction from the corresponding 6,13-diaryl pentacene precursors. The fusion of two indeno-units dramatically changes the electronic properties and chemical reactivity of pentacene and the obtained compounds exhibited exceptionally high photo-stability in the solution, with a half-life time of 11.2 (3a) and 32.0 (3b) days under ambient light and air conditions. Ordered molecular packing with a small π-π stacking distance was observed in the single crystals of 3a and 3b. Our research provides a promising strategy to access stable higher order acenes with controlled molecular order. This journal is",

author = "{Naibi Lakshminarayana}, Arun and Jingjing Chang and Jie Luo and Bin Zheng and Kuo-Wei Huang and Chunyan Chi",

note = "KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: This work was financially supported by a NUS start-up grant (R-143-000-486-133), MOE AcRF grants (R-143-000-510-112 and R-143-000-573-112) and a A*STAR JCO grant (1431AFG100). K.-W. Huang acknowledges financial support from KAUST.",

year = "2015",

doi = "10.1039/c4cc09812a",

language = "English (US)",

volume = "51",

pages = "3604--3607",

journal = "Chem. Commun.",

issn = "1359-7345",

publisher = "Royal Society of Chemistry",

number = "17",

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TY - JOUR

T1 - Bisindeno-annulated pentacenes with exceptionally high photo-stability and ordered molecular packing: Simple synthesis by a regio-selective Scholl reaction

AU - Naibi Lakshminarayana, Arun

AU - Chang, Jingjing

AU - Luo, Jie

AU - Zheng, Bin

AU - Huang, Kuo-Wei

AU - Chi, Chunyan

N1 - KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: This work was financially supported by a NUS start-up grant (R-143-000-486-133), MOE AcRF grants (R-143-000-510-112 and R-143-000-573-112) and a A*STAR JCO grant (1431AFG100). K.-W. Huang acknowledges financial support from KAUST.

PY - 2015

Y1 - 2015

N2 - Bisindeno-annulated pentacenes 3a and 3b were synthesized by a simple regio-selective, FeCl3-mediated Scholl reaction from the corresponding 6,13-diaryl pentacene precursors. The fusion of two indeno-units dramatically changes the electronic properties and chemical reactivity of pentacene and the obtained compounds exhibited exceptionally high photo-stability in the solution, with a half-life time of 11.2 (3a) and 32.0 (3b) days under ambient light and air conditions. Ordered molecular packing with a small π-π stacking distance was observed in the single crystals of 3a and 3b. Our research provides a promising strategy to access stable higher order acenes with controlled molecular order. This journal is

AB - Bisindeno-annulated pentacenes 3a and 3b were synthesized by a simple regio-selective, FeCl3-mediated Scholl reaction from the corresponding 6,13-diaryl pentacene precursors. The fusion of two indeno-units dramatically changes the electronic properties and chemical reactivity of pentacene and the obtained compounds exhibited exceptionally high photo-stability in the solution, with a half-life time of 11.2 (3a) and 32.0 (3b) days under ambient light and air conditions. Ordered molecular packing with a small π-π stacking distance was observed in the single crystals of 3a and 3b. Our research provides a promising strategy to access stable higher order acenes with controlled molecular order. This journal is

UR - http://hdl.handle.net/10754/563948

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U2 - 10.1039/c4cc09812a

DO - 10.1039/c4cc09812a

M3 - Article

SN - 1359-7345

VL - 51

SP - 3604

EP - 3607

JO - Chem. Commun.

JF - Chem. Commun.

IS - 17

ER -

Bisindeno-annulated pentacenes with exceptionally high photo-stability and ordered molecular packing: Simple synthesis by a regio-selective Scholl reaction

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CCDC 1035233: Experimental Crystal Structure Determination : 6,7,15,16-tetrakis(hexyloxy)dibenzo[b,n]rubicene methanol solvate

CCDC 1035232: Experimental Crystal Structure Determination : 6,15-di-t-butyldibenzo[b,n]rubicene dihydrate

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Bisindeno-annulated pentacenes with exceptionally high photo-stability and ordered molecular packing: Simple synthesis by a regio-selective Scholl reaction

Abstract

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Datasets

CCDC 1035233: Experimental Crystal Structure Determination : 6,7,15,16-tetrakis(hexyloxy)dibenzo[b,n]rubicene methanol solvate

CCDC 1035232: Experimental Crystal Structure Determination : 6,15-di-t-butyldibenzo[b,n]rubicene dihydrate

Cite this