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Chromophoric materials; Pyridinium salts; Proton-transfer; Crystal structure
Abstract:
The crystal structures of the 1:1 proton-transfer compounds of the dipolar donor-π-acceptor compound N,N-dimethyl-4-[(E)-2-(4-pyridinyl)vinyl]aniline (1), also named dimethylamino-stilbazole, with 3-nitrophthalic and perchloric acids, viz. (E)-4-[4-(dimethylamino)styryl]pyridinium 2-carboxy-3-nitrobenzoate monohydrate (2) and (E)-4-[4-(dimethylamino)styryl]pyridinium perchlorate (3) are described. A redetermination of the structure of the parent free base 1 at 100 K is also reported. The (E)-4-[4-(dimethylamino)styryl]pyridinium ion exhibits slight whole molecule disorder in 2 and 3. Compound 2 is the first organic salt that contains the unusual monoanion of 3-nitrophthalic acid that is deprotonated at the 1-carboxyl group.
Graphical Abstract
The crystal structures of the 1:1 proton-transfer compounds of the dipolar donor-π-acceptor compound N,N-dimethyl-4-[(E)-2-(4-pyridinyl)vinyl]aniline with 3-nitrophthalic and perchloric acids, viz. (E)-4-[4-(dimethylamino)styryl]pyridinium 2-carboxy-3-nitrobenzoate monohydrate and (E)-4-[4-(dimethylamino)styryl]pyridinium perchlorate are described.
