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Azacyanines of the Pyrrolopyrrole Series
Author(s) -
Marks Timo,
Daltrozzo Ewald,
Zumbusch Andreas
Publication year - 2014
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201304235
Subject(s) - fluorescence , reagent , chelation , boron , yield (engineering) , photochemistry , wavelength , hydrogen , chemistry , excitation wavelength , materials science , inorganic chemistry , organic chemistry , optics , optoelectronics , metallurgy , physics
The reaction of POCl 3 ‐activated, readily soluble diketopyrrolopyrrole (DPP) with 2‐aminoheteroaromatics to yield 1:1 and 1:2 hydrogen chelates is described. Complexation of these hydrogen chelates with boron reagents results in thermally and photochemically stable fluorescent dyes (PP–azacyanines). The 1:2 complexes in particular absorb at long wavelengths and are brightly fluorescing. The rich photophysics of the new compounds are presented. Both the pronounced vibrational fine structure of the S 0 →S 1 transitions and the observed fluorescence phenomena allow detailed conclusions to be made on the correlation between molecular structure and optical properties.