期刊
JOURNAL OF MATERIALS CHEMISTRY C
卷 5, 期 10, 页码 2620-2628出版社
ROYAL SOC CHEMISTRY
DOI: 10.1039/c7tc00276a
关键词
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资金
- National Science Centre, Poland [MAESTRO-2012/06/A/ST5/00216]
- Global Research Laboratory Program through the National Research Foundation (NRF) - Ministry of Science, ICT & Future Planning (Korea) [2014K1A1A2064569]
- ERC [Marches - 278845]
- Polish National Science Centre [DEC-2013/09/B/ST5/03417]
- [DEC-2013/10/A/ST4/00114]
- National Research Foundation of Korea [2014K1A1A2064569] Funding Source: Korea Institute of Science & Technology Information (KISTI), National Science & Technology Information Service (NTIS)
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.
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