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Pyrene–Azobenzene Dyads and Their Photochemistry
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC, Physical Organic Chemistry.
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - Ångström, Physical Chemistry.
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC, Physical Organic Chemistry.
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC, Physical Organic Chemistry.
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2014 (English)In: European Journal of Organic Chemistry, ISSN 1434-193X, E-ISSN 1099-0690, Vol. 2014, no 5, 966-972 p.Article in journal (Refereed) Published
Abstract [en]

The facile synthesis of three new folding azobenzene-pyrene systems 13, connected together by a serendipitously obtained and unpredicted ester linkage, is reported. Additional characterization of the photochemistry of these systems revealed variations in azobenzene photoisomerization (trans-cis and cis-trans) and quenching of pyrene fluorescence, as a result of intra-excitation energy transfer from the pyrene chromophore to an azobenzene. Through the use of aryl substituent electronic effects to tune the absorption properties of the azobenzene relative to the pyrene, we show that efficient photo-switching can be achieved when the trans-azobenzene absorbance band is well separated from that of the pyrene (compound 1), whereas overlap of the corresponding absorbance bands in the cases of 2 and 3 significantly compromises trans-cis isomerization by enhancing cis-trans interconversion.

Place, publisher, year, edition, pages
Weinheim: Wiley-VCH Verlagsgesellschaft, 2014. Vol. 2014, no 5, 966-972 p.
National Category
Chemical Sciences
Research subject
Chemistry
Identifiers
URN: urn:nbn:se:uu:diva-214357DOI: 10.1002/ejoc.201301301ISI: 000331266600008OAI: oai:DiVA.org:uu-214357DiVA: diva2:684724
Available from: 2014-01-08 Created: 2014-01-08 Last updated: 2017-12-06Bibliographically approved

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Lomoth, ReinerLundstedt, AnnaGogoll, AdolfWebb, Matthew JGrennberg, Helena

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