Issue 10, 2017

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

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

Supplementary files

Article information

Article type
Paper
Submitted
17 Jan 2017
Accepted
09 Feb 2017
First published
09 Feb 2017

J. Mater. Chem. C, 2017,5, 2620-2628

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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