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Article: Synthesis and photophysical studies of chiral helical macrocyclic scaffolds via coordination-driven self-assembly of 1,8,9,16-tetraethynyltetraphenylene. Formation of monometallic platinum(II) and dimetallic platinum(II)-ruthenium(II) complexes

TitleSynthesis and photophysical studies of chiral helical macrocyclic scaffolds via coordination-driven self-assembly of 1,8,9,16-tetraethynyltetraphenylene. Formation of monometallic platinum(II) and dimetallic platinum(II)-ruthenium(II) complexes
Authors
Issue Date2010
PublisherAmerican Chemical Society. The Journal's web site is located at http://pubs.acs.org/journals/jacsat/index.html
Citation
Journal Of The American Chemical Society, 2010, v. 132 n. 46, p. 16383-16392 How to Cite?
AbstractThis paper is concerned with the synthesis and reactions of enantiopure 1,8,9,16-tetraethynyltetraphenylene (3). We obtained 3 in 34% yield through four steps starting from 1,8,9,16-tetrahydroxytetraphenylene (2a) via a functional group interconversion strategy. On the basis of this chiral "helical" building block, three rigid helical macrocycles 14, 15, and 22 were designed. Complexes 14 and 15 were constructed via coordination-driven self-assembly with platinum(II) complexes 8 and 9b, while 22 cannot be obtained successfully. Then macrocycle 28 was designed on the structural basis of 22 to which octyl chains were introduced, in the hope of improving the solubility of the complex. Macrocycle 28 was finally formed and was characterized by NMR spectroscopy, elemental analysis, and electrospray mass spectrometry. For the enantiopure 15 and 28, circular dichroism (CD) spectra also exhibited chiral properties. Complexes 27 and 28 both exhibited an intense emission band at 621 nm in acetonitrile at 298 K upon excitation at λ > 420 nm. © 2010 American Chemical Society.
Persistent Identifierhttp://hdl.handle.net/10722/133589
ISSN
2015 Impact Factor: 13.038
2015 SCImago Journal Rankings: 7.123
ISI Accession Number ID
Funding AgencyGrant Number
Croucher Foundation (Hong Kong)
Research Grants Council (Hong Kong) (RGC)CUHK403909
Chinese Academy of SciencesGJHZ200816
University Grants Committee Areas of Excellence SchemeAoE/P-03/08
Science and Technology Commission of the Shanghai Municipal Government
Funding Information:

Dedicated to Professor Eiichi Nakamura on the occasion of his 60th birthday. The Institute of Molecular Functional Materials is an Area of Excellence under the University Grants Committee (Hong Kong). This work was supported by a grant from the Croucher Foundation (Hong Kong), a General Research Fund from Research Grants Council (Hong Kong) (RGC ref. No. CUHK403909), the External Cooperation Program of the Chinese Academy of Sciences (BGrant No GJHZ200816), and the University Grants Committee Areas of Excellence Scheme (AoE/P-03/08). F.L. acknowledges with thanks the Croucher Foundation (Hong Kong) for a Shanghai Studentship. The Science and Technology Commission of the Shanghai Municipal Government also partially supported this program. We thank Professors Li-Xin Dai and Xue-Long Hou for helpful discussions.

References
Grants

 

DC FieldValueLanguage
dc.contributor.authorLin, Fen_HK
dc.contributor.authorPeng, HYen_HK
dc.contributor.authorChen, JXen_HK
dc.contributor.authorChik, DTWen_HK
dc.contributor.authorCai, Zen_HK
dc.contributor.authorWong, KMCen_HK
dc.contributor.authorYam, VWWen_HK
dc.contributor.authorWong, HNCen_HK
dc.date.accessioned2011-05-24T02:11:31Z-
dc.date.available2011-05-24T02:11:31Z-
dc.date.issued2010en_HK
dc.identifier.citationJournal Of The American Chemical Society, 2010, v. 132 n. 46, p. 16383-16392en_HK
dc.identifier.issn0002-7863en_HK
dc.identifier.urihttp://hdl.handle.net/10722/133589-
dc.description.abstractThis paper is concerned with the synthesis and reactions of enantiopure 1,8,9,16-tetraethynyltetraphenylene (3). We obtained 3 in 34% yield through four steps starting from 1,8,9,16-tetrahydroxytetraphenylene (2a) via a functional group interconversion strategy. On the basis of this chiral "helical" building block, three rigid helical macrocycles 14, 15, and 22 were designed. Complexes 14 and 15 were constructed via coordination-driven self-assembly with platinum(II) complexes 8 and 9b, while 22 cannot be obtained successfully. Then macrocycle 28 was designed on the structural basis of 22 to which octyl chains were introduced, in the hope of improving the solubility of the complex. Macrocycle 28 was finally formed and was characterized by NMR spectroscopy, elemental analysis, and electrospray mass spectrometry. For the enantiopure 15 and 28, circular dichroism (CD) spectra also exhibited chiral properties. Complexes 27 and 28 both exhibited an intense emission band at 621 nm in acetonitrile at 298 K upon excitation at λ > 420 nm. © 2010 American Chemical Society.en_HK
dc.languageengen_US
dc.publisherAmerican Chemical Society. The Journal's web site is located at http://pubs.acs.org/journals/jacsat/index.htmlen_HK
dc.relation.ispartofJournal of the American Chemical Societyen_HK
dc.titleSynthesis and photophysical studies of chiral helical macrocyclic scaffolds via coordination-driven self-assembly of 1,8,9,16-tetraethynyltetraphenylene. Formation of monometallic platinum(II) and dimetallic platinum(II)-ruthenium(II) complexesen_HK
dc.typeArticleen_HK
dc.identifier.openurlhttp://library.hku.hk:4550/resserv?sid=HKU:IR&issn=0002-7863&volume=132&issue=46&spage=16383&epage=16392&date=2010&atitle=Synthesis+and+photophysical+studies+of+chiral+helical+macrocyclic+scaffolds+via+coordination-driven+self-assembly+of+1,8,9,16-tetraethynyltetraphenylene.+formation+of+monometallic+platinum(ii)+and+dimetallic+platinum(ii)−ruthenium(ii)+complexes-
dc.identifier.emailWong, KMC:wongmc@hku.hken_HK
dc.identifier.emailYam, VWW:wwyam@hku.hken_HK
dc.identifier.authorityWong, KMC=rp00809en_HK
dc.identifier.authorityYam, VWW=rp00822en_HK
dc.description.naturelink_to_subscribed_fulltext-
dc.identifier.doi10.1021/ja106599jen_HK
dc.identifier.pmid21033663-
dc.identifier.scopuseid_2-s2.0-78649259654en_HK
dc.identifier.hkuros185248en_US
dc.relation.referenceshttp://www.scopus.com/mlt/select.url?eid=2-s2.0-78649259654&selection=ref&src=s&origin=recordpageen_HK
dc.identifier.volume132en_HK
dc.identifier.issue46en_HK
dc.identifier.spage16383en_HK
dc.identifier.epage16392en_HK
dc.identifier.isiWOS:000284792000029-
dc.publisher.placeUnited Statesen_HK
dc.relation.projectInstitute of Molecular Functional Materials-
dc.identifier.scopusauthoridLin, F=36698926600en_HK
dc.identifier.scopusauthoridPeng, HY=36698943700en_HK
dc.identifier.scopusauthoridChen, JX=36698794700en_HK
dc.identifier.scopusauthoridChik, DTW=7801376808en_HK
dc.identifier.scopusauthoridCai, Z=7402904946en_HK
dc.identifier.scopusauthoridWong, KMC=8061067200en_HK
dc.identifier.scopusauthoridYam, VWW=18539304700en_HK
dc.identifier.scopusauthoridWong, HNC=7402864789en_HK

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