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dc.contributor.authorPurc, Anna
dc.contributor.authorKoszarna, Beata
dc.contributor.authorIachina, Irina
dc.contributor.authorFriese, Daniel Henrik
dc.contributor.authorTasior, Mariusz
dc.contributor.authorSobczyk, Krzysztof
dc.contributor.authorPedzinski, Tomasz
dc.contributor.authorBrewer, Jonathan
dc.contributor.authorGryko, Daniel T
dc.date.accessioned2022-06-03T11:00:21Z
dc.date.available2022-06-03T11:00:21Z
dc.date.issued2017-02-07
dc.description.abstractAn in-depth investigation of the reaction of substituted salicylaldehydes with chloroacetonitrile led to the development of new conditions for the synthesis of 2-cyanobenzofurans. The crucial improvement lies in the use of phase-transfer catalysis in the second step, i.e., intramolecular aldol type condensation. In a two-step process, the reactants were transformed into a library of 3,6-bis(benzofuran-2-yl)diketopyrrolopyrroles. We show that the presence of a methyl group in a position adjacent to the cyano functionality only slightly decreased the yield of diketopyrrolopyrroles (to 30–57%). An analysis of the relationship between the degree of polarization/planarization of aryl-diketopyrrolopyrroles and their one- and twophoton spectroscopic properties is reported. Careful design of the desired dyes and enhanced control of their ability to assume a planar molecular structure resulted in interesting photophysical properties, such as absorption and emission in the so-called biological window. Despite having less promising linear spectroscopic properties, the deplanarized molecules possess pretty strong two-photon absorbing properties. Placing methyl groups at adjacent positions to the linkage between benzofuran and the DPP core caused the formation of yellow-emitting dyes with almost quantitative fluorescence quantum yield, moderate Stokes shift and reasonable two-photon absorption cross-sections.en_US
dc.identifier.citationPurc, Koszarna, Iachina, Friese DH, Tasior, Sobczyk, Pedzinski, Brewer, Gryko. The impact of interplay between electronic and steric effects on the synthesis and the linear and non-linear optical properties of diketopyrrolopyrrole bearing benzofuran moieties. Organic Chemistry Frontiers. 2017;4(5):724-736en_US
dc.identifier.cristinIDFRIDAID 1543071
dc.identifier.doi10.1039/c6qo00869k
dc.identifier.issn2052-4110
dc.identifier.issn2052-4129
dc.identifier.urihttps://hdl.handle.net/10037/25371
dc.language.isoengen_US
dc.publisherRoyal Society of Chemistryen_US
dc.relation.journalOrganic Chemistry Frontiers
dc.rights.accessRightsopenAccessen_US
dc.rights.holderCopyright 2017 The Partner Organisationsen_US
dc.titleThe impact of interplay between electronic and steric effects on the synthesis and the linear and non-linear optical properties of diketopyrrolopyrrole bearing benzofuran moietiesen_US
dc.type.versionpublishedVersionen_US
dc.typeJournal articleen_US
dc.typeTidsskriftartikkelen_US
dc.typePeer revieweden_US


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