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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

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Abstract

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.

Graphical abstract: 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

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Publication details

The article was received on 29 Dec 2016, accepted on 30 Jan 2017 and first published on 07 Feb 2017


Article type: Research Article
DOI: 10.1039/C6QO00869K
Citation: Org. Chem. Front., 2017, Advance Article
  • Open access: Creative Commons BY license
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    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

    A. Purc, B. Koszarna, I. Iachina, D. H. Friese, M. Tasior, K. Sobczyk, T. Pędziński, J. Brewer and D. T. Gryko, Org. Chem. Front., 2017, Advance Article , DOI: 10.1039/C6QO00869K

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