Pyrene–Azobenzene Dyads and Their Photochemistry
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
The facile synthesis of three new folding azobenzene-pyrene systems 1–3, 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.
Research subject Chemistry
IdentifiersURN: urn:nbn:se:uu:diva-214357DOI: 10.1002/ejoc.201301301ISI: 000331266600008OAI: oai:DiVA.org:uu-214357DiVA: diva2:684724