Palladium-Catalyzed Direct C-H Arylations of Dioxythiophenes Bearing Reactive Functional Groups: A Step-Economical Approach for Functional π-Conjugated Oligoarenes

Handle URI:
http://hdl.handle.net/10754/558679
Title:
Palladium-Catalyzed Direct C-H Arylations of Dioxythiophenes Bearing Reactive Functional Groups: A Step-Economical Approach for Functional π-Conjugated Oligoarenes
Authors:
Liu, Ching-Yuan; Chong, Hui; Lin, Hsing-An; Yamashita, Yoshiro; Zheng, Bin; Huang, Kuo-Wei ( 0000-0003-1900-2658 ) ; Hashizume, Daisuke; Yu, Hsiao-hua
Abstract:
A Pd-catalyzed and single-step C-H arylation of dioxythiophene derivates bearing unprotected reactive functional groups (-OH, -COOH, -N3) in a phosphine-free manner has been developed. Various dioxythiopene-based oligoarenes with extended π-conjugation are obtained with good yields (up to 90%). These oligoarenes display suitable optical properties (absorption and emission maxima, quantum yields) and contain reactive functional groups suitable for further conjugations with bioactive molecules. This new methodology is step economical (fewer synthetic steps), environmental friendly (no toxic metal-containing side-poducts) and the oligoarenes synthesized are potentially applicable for bio-labeling, bioimaging, and biosensing.
KAUST Department:
KAUST Catalysis Center (KCC); Physical Sciences and Engineering (PSE) Division
Citation:
Palladium-Catalyzed Direct C-H Arylations of Dioxythiophenes Bearing Reactive Functional Groups: A Step-Economical Approach for Functional π-Conjugated Oligoarenes 2015 Org. Biomol. Chem.
Publisher:
Royal Society of Chemistry (RSC)
Journal:
Org. Biomol. Chem.
Issue Date:
25-Jun-2015
DOI:
10.1039/C5OB00705D
Type:
Article
ISSN:
1477-0520; 1477-0539
Is Supplemented By:
Liu, C.-Y., Chong, H., Lin, H.-A., Yamashita, Y., Zhang, B., Huang, K.-W., … Yu, H.-H. (2015). CCDC 1055679: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/cc14fj58; DOI:10.5517/cc14fj58; HANDLE:http://hdl.handle.net/10754/624421; Liu, C.-Y., Chong, H., Lin, H.-A., Yamashita, Y., Zhang, B., Huang, K.-W., … Yu, H.-H. (2015). CCDC 1055680: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/cc14fj69; DOI:10.5517/cc14fj69; HANDLE:http://hdl.handle.net/10754/624422; Liu, C.-Y., Chong, H., Lin, H.-A., Yamashita, Y., Zhang, B., Huang, K.-W., … Yu, H.-H. (2015). CCDC 1055681: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/cc14fj7b; DOI:10.5517/cc14fj7b; HANDLE:http://hdl.handle.net/10754/624423
Additional Links:
http://pubs.rsc.org/en/Content/ArticleLanding/2015/OB/C5OB00705D
Appears in Collections:
Articles; Physical Sciences and Engineering (PSE) Division; KAUST Catalysis Center (KCC)

Full metadata record

DC FieldValue Language
dc.contributor.authorLiu, Ching-Yuanen
dc.contributor.authorChong, Huien
dc.contributor.authorLin, Hsing-Anen
dc.contributor.authorYamashita, Yoshiroen
dc.contributor.authorZheng, Binen
dc.contributor.authorHuang, Kuo-Weien
dc.contributor.authorHashizume, Daisukeen
dc.contributor.authorYu, Hsiao-huaen
dc.date.accessioned2015-06-30T14:17:30Zen
dc.date.available2015-06-30T14:17:30Zen
dc.date.issued2015-06-25en
dc.identifier.citationPalladium-Catalyzed Direct C-H Arylations of Dioxythiophenes Bearing Reactive Functional Groups: A Step-Economical Approach for Functional π-Conjugated Oligoarenes 2015 Org. Biomol. Chem.en
dc.identifier.issn1477-0520en
dc.identifier.issn1477-0539en
dc.identifier.doi10.1039/C5OB00705Den
dc.identifier.urihttp://hdl.handle.net/10754/558679en
dc.description.abstractA Pd-catalyzed and single-step C-H arylation of dioxythiophene derivates bearing unprotected reactive functional groups (-OH, -COOH, -N3) in a phosphine-free manner has been developed. Various dioxythiopene-based oligoarenes with extended π-conjugation are obtained with good yields (up to 90%). These oligoarenes display suitable optical properties (absorption and emission maxima, quantum yields) and contain reactive functional groups suitable for further conjugations with bioactive molecules. This new methodology is step economical (fewer synthetic steps), environmental friendly (no toxic metal-containing side-poducts) and the oligoarenes synthesized are potentially applicable for bio-labeling, bioimaging, and biosensing.en
dc.publisherRoyal Society of Chemistry (RSC)en
dc.relation.urlhttp://pubs.rsc.org/en/Content/ArticleLanding/2015/OB/C5OB00705Den
dc.rightsArchived with thanks to Org. Biomol. Chem.en
dc.titlePalladium-Catalyzed Direct C-H Arylations of Dioxythiophenes Bearing Reactive Functional Groups: A Step-Economical Approach for Functional π-Conjugated Oligoarenesen
dc.typeArticleen
dc.contributor.departmentKAUST Catalysis Center (KCC)en
dc.contributor.departmentPhysical Sciences and Engineering (PSE) Divisionen
dc.identifier.journalOrg. Biomol. Chem.en
dc.eprint.versionPost-printen
dc.contributor.institutionResponsive Organic Materials Laboratory, RIKEN, 2 ‐ 1 Hirosawa, Wako, Saitama 351 ‐ 0198, Japanen
dc.contributor.institutionDepartment of Chemical and Material Engineering, National Central University, Jhongli City, Taoyuan 32001, Taiwanen
dc.contributor.institutionDepartment of Electronic Chemistry, Interdisciplinary Graduate School of Science and Engineering, Tokyo Institute of Technology, Japanen
dc.contributor.institutionMaterials Characterization Support Unit, RIKEN Center for Emergent Matter Science, Japanen
dc.contributor.institutionInstitute of Chemistry, Academia Sinica, 128 Academic Road, Sec. 2, Nankang, Taipei 11529, Taiwan. Email: bruceyu@gate.sinica.edu.tw; Tel: +886 ‐ 2 ‐ 2789 ‐ 8634en
kaust.authorZhang, Binen
kaust.authorHuang, Kuo-Weien
dc.relation.isSupplementedByLiu, C.-Y., Chong, H., Lin, H.-A., Yamashita, Y., Zhang, B., Huang, K.-W., … Yu, H.-H. (2015). CCDC 1055679: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/cc14fj58en
dc.relation.isSupplementedByDOI:10.5517/cc14fj58en
dc.relation.isSupplementedByHANDLE:http://hdl.handle.net/10754/624421en
dc.relation.isSupplementedByLiu, C.-Y., Chong, H., Lin, H.-A., Yamashita, Y., Zhang, B., Huang, K.-W., … Yu, H.-H. (2015). CCDC 1055680: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/cc14fj69en
dc.relation.isSupplementedByDOI:10.5517/cc14fj69en
dc.relation.isSupplementedByHANDLE:http://hdl.handle.net/10754/624422en
dc.relation.isSupplementedByLiu, C.-Y., Chong, H., Lin, H.-A., Yamashita, Y., Zhang, B., Huang, K.-W., … Yu, H.-H. (2015). CCDC 1055681: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/cc14fj7ben
dc.relation.isSupplementedByDOI:10.5517/cc14fj7ben
dc.relation.isSupplementedByHANDLE:http://hdl.handle.net/10754/624423en
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