Journal
CHEMISTRY-AN ASIAN JOURNAL
Volume 6, Issue 4, Pages 1026-1037Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/asia.201000641
Keywords
BODIPYs; density functional theory; dyes/pigments; fluorescence; IR spectroscopy
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Funding
- National Natural Science Foundation of China [20971066, 21021062]
- Chinese Ministry of Education [NCET-080-0272]
- Major State Basic Research Development Program of China [2011CB808704, 2007CB925103]
- Japanese Ministry of Education, Culture, Sports, Science, and Technology (MEXT) [20108007]
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A series of fused-ring-expanded aza-boradiazaindacene (aza-BODIPY) dyes have been synthesized by reacting arylmagnesium bromides with phthalonitriles or naphthalenedicarbonitriles. An analysis of the structure-property relationships has been carried out based on X-ray crystallography, optical spectroscopy, and theoretical calculations. Benzo and 1,2-naphtho-fused 3,5-diaryl aza-BODIPY dyes display markedly red shifted absorption and emission bands in the near-IR region (>700 nm) due to changes in the energies of the frontier MOs relative to those of 1,3,5,7-tetraaryl aza-BODIPYs. Only one 1,2-naphtho-fused aza-BODIPY of the three possible isomers is formed due to steric effects, and 2,3-naphtho-fused compounds could not be characterized because the final BF2 complexes are unstable in solution. The incorporation of a -N(CH3)(2) group at the para-positions of a benzo-fused 3,5-diaryl aza-BODIPY quenches the fluorescence in polar solvents and results in a ratiometric pH response, which could be used in future practical applications as an NIR turn-on fluorescence sensor.
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