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Design and Characterization of 4,5‐Bis(diarylamino)phthalic Acid Diesters as a New Class of Fluorophores Exhibiting Efficient Blue Emission in the Solid State
Author(s) -
Shimizu Masaki,
Tamagawa Tomokazu
Publication year - 2015
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201403272
Subject(s) - bathochromic shift , chemistry , phthalic acid , intramolecular force , fluorescence , photoluminescence , photochemistry , density functional theory , polymer chemistry , computational chemistry , organic chemistry , physics , quantum mechanics , optics
We developed 4,5‐bis(diarylamino)phthalic acid diesters as blue fluorophores exhibiting efficient photoluminescence in powder and in a thin film of pol(methyl methacrylate). Increasing the electron‐donating nature of the substituents in the para positions of the diarylamino moieties in the dimethyl esters increased the redshift in the fluorescence spectrum. Replacing the methoxycarbonyl groups with aryloxylcarbonyl groups also induced a bathochromic shift in the fluorescence spectrum. Thus, the color of the emission was finely tuned by simple molecular modification. Single‐crystal X‐ray analysis revealed a twisted conformation with loose packing in the crystal. Density functional theory calculations suggested that the excitation process was governed by intramolecular charge transfer from the diarylamino moieties to the alkoxycarbonyl groups.