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

作者：Purc Anna; Koszarna Beata; Iachina Irina; Friese Daniel H; Tasior Mariusz; Sobczyk Krzysztof; Pedzinski Tomasz; Brewer Jonathan; Gryko Daniel T

来源：Organic Chemistry Frontiers, 2017, 4(5): 724-736.

DOI：10.1039/c6qo00869k

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 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.

• 出版日期2017-5-1