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Article: Thermo- And acid-responsive photochromic spironaphthoxazine containing organogelators

TitleThermo- And acid-responsive photochromic spironaphthoxazine containing organogelators
Authors
KeywordsAcidichromism
Organogels
Photochromism
Spironaphthoxazine
Supramolecular chemistry
Issue Date2010
PublisherWiley - V C H Verlag GmbH & Co KGaA. The Journal's web site is located at http://www.wiley-vch.de/home/chemistry
Citation
Chemistry - A European Journal, 2010, v. 16 n. 29, p. 8690-8698 How to Cite?
AbstractA series of photochromic spironaphthoxazine derivatives has been designed, synthesized, and characterized by using 1H NMR spectroscopy, FAB mass spectrometry, and elemental analysis. Their photophysical and photochromic behavior have been investigated. Two of the compounds (G12-enSA-SO and G16-en-SA-SO) have been shown to be capable of forming stable thermoreversible organogels in organic solvents, tested by the "stable-to-inversion of a test tube" method. Addition of p-toluenesulfonic acid was found to induce the formation of stable organogels at concentrations below that of the critical gelation concentration (c.g.c), with a concomitant change in color from colorless to purple. Transmission electron microscopy and scanning electron microscopy of the xerogels showed typical fibrous structures in the micrometer scale. The activation parameters for the bleaching reaction of G8-en-SA-SO in the solution state and G 16-en-SA-SO in the gel state have been determined in ethanol through kinetic studies at various temperatures. The results showed that the rate of the bleaching reaction in the gel state was much slower than that in the solution state. © 2010 Wiley-VCH Verlag GmbH & Cu. KGaA. Weinheim.
Persistent Identifierhttp://hdl.handle.net/10722/124536
ISSN
2015 Impact Factor: 5.771
2015 SCImago Journal Rankings: 2.323
ISI Accession Number ID
Funding AgencyGrant Number
University of Hong Kong
Jilin University
University Grants Committee (Hong Kong)AoE/P-03/08
Natural Science Foundation of China
Research Grants Council of Hong Kong Joint Research Scheme (NSFC-RGC)N_HKU 737/06
Funding Information:

V.W.-WY. acknowledges support from The University of Hong Kong under the Distinguished Research Achievement Award Scheme. We also acknowledge support from Jilin University and the University of Hong Kong. This work has been supported by the Areas of Excellence Scheme, University Grants Committee (Hong Kong) (work at the Institute of Molecular Materials; grant no. AoE/P-03/08) and the Natural Science Foundation of China and the Research Grants Council of Hong Kong Joint Research Scheme (NSFC-RGC Project No. N_HKU 737/06). A.Y.-Y.T. acknowledges the receipt of a University Postdoctoral Fellowship from The University of Hong Kong.

References
Grants

 

DC FieldValueLanguage
dc.contributor.authorLi, Yen_HK
dc.contributor.authorWong, KMCen_HK
dc.contributor.authorTam, AYYen_HK
dc.contributor.authorWu, Len_HK
dc.contributor.authorYam, VWWen_HK
dc.date.accessioned2010-10-31T10:40:01Z-
dc.date.available2010-10-31T10:40:01Z-
dc.date.issued2010en_HK
dc.identifier.citationChemistry - A European Journal, 2010, v. 16 n. 29, p. 8690-8698en_HK
dc.identifier.issn0947-6539en_HK
dc.identifier.urihttp://hdl.handle.net/10722/124536-
dc.description.abstractA series of photochromic spironaphthoxazine derivatives has been designed, synthesized, and characterized by using 1H NMR spectroscopy, FAB mass spectrometry, and elemental analysis. Their photophysical and photochromic behavior have been investigated. Two of the compounds (G12-enSA-SO and G16-en-SA-SO) have been shown to be capable of forming stable thermoreversible organogels in organic solvents, tested by the "stable-to-inversion of a test tube" method. Addition of p-toluenesulfonic acid was found to induce the formation of stable organogels at concentrations below that of the critical gelation concentration (c.g.c), with a concomitant change in color from colorless to purple. Transmission electron microscopy and scanning electron microscopy of the xerogels showed typical fibrous structures in the micrometer scale. The activation parameters for the bleaching reaction of G8-en-SA-SO in the solution state and G 16-en-SA-SO in the gel state have been determined in ethanol through kinetic studies at various temperatures. The results showed that the rate of the bleaching reaction in the gel state was much slower than that in the solution state. © 2010 Wiley-VCH Verlag GmbH & Cu. KGaA. Weinheim.en_HK
dc.languageengen_HK
dc.publisherWiley - V C H Verlag GmbH & Co KGaA. The Journal's web site is located at http://www.wiley-vch.de/home/chemistryen_HK
dc.relation.ispartofChemistry - A European Journalen_HK
dc.subjectAcidichromismen_HK
dc.subjectOrganogelsen_HK
dc.subjectPhotochromismen_HK
dc.subjectSpironaphthoxazineen_HK
dc.subjectSupramolecular chemistryen_HK
dc.titleThermo- And acid-responsive photochromic spironaphthoxazine containing organogelatorsen_HK
dc.typeArticleen_HK
dc.identifier.openurlhttp://library.hku.hk:4550/resserv?sid=HKU:IR&issn=0947-6539&volume=16&issue=29&spage=8690&epage=8698&date=2010&atitle=Thermo-+and+acid-responsive+photochromic+spironaphthoxazine-containing+organogelators-
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.doi10.1002/chem.201000150en_HK
dc.identifier.pmid20583051-
dc.identifier.scopuseid_2-s2.0-77955154484en_HK
dc.identifier.hkuros175556en_HK
dc.relation.referenceshttp://www.scopus.com/mlt/select.url?eid=2-s2.0-77955154484&selection=ref&src=s&origin=recordpageen_HK
dc.identifier.volume16en_HK
dc.identifier.issue29en_HK
dc.identifier.spage8690en_HK
dc.identifier.epage8698en_HK
dc.identifier.isiWOS:000281060800017-
dc.publisher.placeGermanyen_HK
dc.relation.projectSynthesis, aggregation and self-assembly of luminescent functional molecules - from solutions to polymers, ordered thin films, inorganic-organic hybrids, and supramolecular and nano-assemblies-
dc.relation.projectInstitute of Molecular Functional Materials-
dc.identifier.scopusauthoridLi, Y=36349372200en_HK
dc.identifier.scopusauthoridWong, KMC=8061067200en_HK
dc.identifier.scopusauthoridTam, AYY=16643873800en_HK
dc.identifier.scopusauthoridWu, L=7404902949en_HK
dc.identifier.scopusauthoridYam, VWW=18539304700en_HK

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