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Issue 10, 2017
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2,5-Bis(azulenyl)pyrrolo[3,2-b]pyrroles – the key influence of the linkage position on the linear and nonlinear optical properties

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Abstract

The first route towards pyrrolo[3,2-b]pyrroles containing two azulene moieties at positions 2 and 5 was developed. The key step of this approach is the three-step transformation of pyridine scaffolds into azulene via sequential N-arylation followed by ring-opening and a reaction with cyclopentadiene. The resulting quadrupolar acceptor–donor–acceptor compounds possess interesting optical properties such as bathochromically shifted absorption with the magnitude of the red-shift strongly dependent on the linkage position. Two-photon absorption of these functional dyes is markedly different from that of previously described pyrrolo[3,2-b]pyrroles. The experimental optical spectra were rationalized using time-dependent density functional theory calculations of both the linear and nonlinear optical properties.

Graphical abstract: 2,5-Bis(azulenyl)pyrrolo[3,2-b]pyrroles – the key influence of the linkage position on the linear and nonlinear optical properties

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Publication details

The article was received on 17 Jan 2017, accepted on 09 Feb 2017 and first published on 09 Feb 2017


Article type: Paper
DOI: 10.1039/C7TC00276A
Citation: J. Mater. Chem. C, 2017,5, 2620-2628
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    2,5-Bis(azulenyl)pyrrolo[3,2-b]pyrroles – the key influence of the linkage position on the linear and nonlinear optical properties

    Y. M. Poronik, L. M. Mazur, M. Samoć, D. Jacquemin and D. T. Gryko, J. Mater. Chem. C, 2017, 5, 2620
    DOI: 10.1039/C7TC00276A

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