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

Anna Purc, Beata Koszarna, Irina Iachina, Daniel H. Friese, Mariusz Tasior, Krzysztof Sobczyk, Tomasz Pȩdziński, Jonathan Brewer, Daniel T. Gryko*

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Abstrakt

An 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 two-photon 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.

OriginalsprogEngelsk
TidsskriftOrganic Chemistry Frontiers
Vol/bind4
Udgave nummer5
Sider (fra-til)724-736
ISSN2052-4129
DOI
StatusUdgivet - 2017

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