meso-Substituted bisanthenes as soluble and stable near-infrared dyes

Handle URI:
http://hdl.handle.net/10754/575536
Title:
meso-Substituted bisanthenes as soluble and stable near-infrared dyes
Authors:
Li, Jinling; Zhang, Kai; Zhang, Xiaojie; Huang, Kuo-Wei ( 0000-0003-1900-2658 ) ; Chi, Chunyan; Wu, Jishan
Abstract:
(Chemical Equation Presented) Three meso-substituted bisanthenes, 4-6, were prepared in a short synthetic route from the bisanthenequinone. They exhibit largely improved stability and solubility in comparison to the parent bisanthene. All of these compounds also show near-infrared (NIR) absorption and emission with high to moderate fluorescence quantum yields. Amphoteric redox behavior was observed for 4-6 by cyclic voltammetry, and these compounds can be reversibly oxidized and reduced into respective cationic and anionic species by both electrochemical and chemical processes. In addition, compound 5 adopts a herringbone π-stacking motif in the single crystal. © 2010 American Chemical Society.
KAUST Department:
Biological and Environmental Sciences and Engineering (BESE) Division; KAUST Catalysis Center (KCC); Physical Sciences and Engineering (PSE) Division; Chemical Science Program; Homogeneous Catalysis Laboratory (HCL)
Publisher:
American Chemical Society (ACS)
Journal:
The Journal of Organic Chemistry
Issue Date:
5-Feb-2010
DOI:
10.1021/jo902413h
PubMed ID:
20055372
Type:
Article
ISSN:
00223263
Sponsors:
This work was financially supported by the NRF Competitive Research Program (R-143-000-360281) and NUS Young Investigator Award (R-143-000-356101).
Is Supplemented By:
Li, J., Zhang, K., Zhang, X., Huang, K.-W., Chi, C., & Wu, J. (2011). CCDC 812853: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/ccw8v21; DOI:10.5517/ccw8v21; HANDLE:http://hdl.handle.net/10754/624633
Appears in Collections:
Articles; Physical Sciences and Engineering (PSE) Division; Chemical Science Program; KAUST Catalysis Center (KCC); Biological and Environmental Sciences and Engineering (BESE) Division

Full metadata record

DC FieldValue Language
dc.contributor.authorLi, Jinlingen
dc.contributor.authorZhang, Kaien
dc.contributor.authorZhang, Xiaojieen
dc.contributor.authorHuang, Kuo-Weien
dc.contributor.authorChi, Chunyanen
dc.contributor.authorWu, Jishanen
dc.date.accessioned2015-08-24T08:32:10Zen
dc.date.available2015-08-24T08:32:10Zen
dc.date.issued2010-02-05en
dc.identifier.issn00223263en
dc.identifier.pmid20055372en
dc.identifier.doi10.1021/jo902413hen
dc.identifier.urihttp://hdl.handle.net/10754/575536en
dc.description.abstract(Chemical Equation Presented) Three meso-substituted bisanthenes, 4-6, were prepared in a short synthetic route from the bisanthenequinone. They exhibit largely improved stability and solubility in comparison to the parent bisanthene. All of these compounds also show near-infrared (NIR) absorption and emission with high to moderate fluorescence quantum yields. Amphoteric redox behavior was observed for 4-6 by cyclic voltammetry, and these compounds can be reversibly oxidized and reduced into respective cationic and anionic species by both electrochemical and chemical processes. In addition, compound 5 adopts a herringbone π-stacking motif in the single crystal. © 2010 American Chemical Society.en
dc.description.sponsorshipThis work was financially supported by the NRF Competitive Research Program (R-143-000-360281) and NUS Young Investigator Award (R-143-000-356101).en
dc.publisherAmerican Chemical Society (ACS)en
dc.titlemeso-Substituted bisanthenes as soluble and stable near-infrared dyesen
dc.typeArticleen
dc.contributor.departmentBiological and Environmental Sciences and Engineering (BESE) Divisionen
dc.contributor.departmentKAUST Catalysis Center (KCC)en
dc.contributor.departmentPhysical Sciences and Engineering (PSE) Divisionen
dc.contributor.departmentChemical Science Programen
dc.contributor.departmentHomogeneous Catalysis Laboratory (HCL)en
dc.identifier.journalThe Journal of Organic Chemistryen
dc.contributor.institutionDepartment of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore 117543, Singaporeen
kaust.authorHuang, Kuo-Weien
dc.relation.isSupplementedByLi, J., Zhang, K., Zhang, X., Huang, K.-W., Chi, C., & Wu, J. (2011). CCDC 812853: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/ccw8v21en
dc.relation.isSupplementedByDOI:10.5517/ccw8v21en
dc.relation.isSupplementedByHANDLE:http://hdl.handle.net/10754/624633en

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