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

Handle URI:
http://hdl.handle.net/10754/563948
Title:
Bisindeno-annulated pentacenes with exceptionally high photo-stability and ordered molecular packing: Simple synthesis by a regio-selective Scholl reaction
Authors:
Naibi Lakshminarayana, Arun; Chang, Jingjing; Luo, Jie; Zheng, Bin; Huang, Kuo-Wei ( 0000-0003-1900-2658 ) ; Chi, Chunyan
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
KAUST Department:
KAUST Catalysis Center (KCC); Physical Sciences and Engineering (PSE) Division; Chemical Science Program; HCL
Publisher:
Royal Society of Chemistry (RSC)
Journal:
Chem. Commun.
Issue Date:
2015
DOI:
10.1039/c4cc09812a
Type:
Article
ISSN:
13597345
Sponsors:
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.
Is Supplemented By:
Lakshminarayana, A. N., Chang, J., Luo, J., Zheng, B., Huang, K.-W., & Chi, C. (2015). CCDC 1035232: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/cc13r7lp; DOI:10.5517/cc13r7lp; HANDLE:http://hdl.handle.net/10754/624380; Lakshminarayana, A. N., Chang, J., Luo, J., Zheng, B., Huang, K.-W., & Chi, C. (2015). CCDC 1035233: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/cc13r7mq; DOI:10.5517/cc13r7mq; HANDLE:http://hdl.handle.net/10754/624381
Appears in Collections:
Articles; Physical Sciences and Engineering (PSE) Division; Chemical Science Program; KAUST Catalysis Center (KCC)

Full metadata record

DC FieldValue Language
dc.contributor.authorNaibi Lakshminarayana, Arunen
dc.contributor.authorChang, Jingjingen
dc.contributor.authorLuo, Jieen
dc.contributor.authorZheng, Binen
dc.contributor.authorHuang, Kuo-Weien
dc.contributor.authorChi, Chunyanen
dc.date.accessioned2015-08-03T12:20:33Zen
dc.date.available2015-08-03T12:20:33Zen
dc.date.issued2015en
dc.identifier.issn13597345en
dc.identifier.doi10.1039/c4cc09812aen
dc.identifier.urihttp://hdl.handle.net/10754/563948en
dc.description.abstractBisindeno-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 isen
dc.description.sponsorshipThis 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.en
dc.publisherRoyal Society of Chemistry (RSC)en
dc.titleBisindeno-annulated pentacenes with exceptionally high photo-stability and ordered molecular packing: Simple synthesis by a regio-selective Scholl reactionen
dc.typeArticleen
dc.contributor.departmentKAUST Catalysis Center (KCC)en
dc.contributor.departmentPhysical Sciences and Engineering (PSE) Divisionen
dc.contributor.departmentChemical Science Programen
dc.contributor.departmentHCLen
dc.identifier.journalChem. Commun.en
dc.contributor.institutionDepartment of Chemistry, National University of Singapore, 3 Science Drive 3Singapore, Singaporeen
dc.contributor.institutionInstitute of Materials Research and Engineering, A Star 3 Research LinkSingapore, Singaporeen
kaust.authorZheng, Binen
kaust.authorHuang, Kuo-Weien
dc.relation.isSupplementedByLakshminarayana, A. N., Chang, J., Luo, J., Zheng, B., Huang, K.-W., & Chi, C. (2015). CCDC 1035232: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/cc13r7lpen
dc.relation.isSupplementedByDOI:10.5517/cc13r7lpen
dc.relation.isSupplementedByHANDLE:http://hdl.handle.net/10754/624380en
dc.relation.isSupplementedByLakshminarayana, A. N., Chang, J., Luo, J., Zheng, B., Huang, K.-W., & Chi, C. (2015). CCDC 1035233: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/cc13r7mqen
dc.relation.isSupplementedByDOI:10.5517/cc13r7mqen
dc.relation.isSupplementedByHANDLE:http://hdl.handle.net/10754/624381en
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