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Photochemical behavior of micellized 4‐(4′‐alkylstyryl)pyridinium salts
Author(s) -
Koźlecki Tomasz,
Wilk Kazimiera A.
Publication year - 1996
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/(sici)1099-1395(199609)9:9<645::aid-poc830>3.0.co;2-9
Subject(s) - chemistry , photochromism , steric effects , pyridinium , isomerization , photochemistry , alkyl , micelle , halide , counterion , irradiation , iodide , ion , medicinal chemistry , stereochemistry , organic chemistry , aqueous solution , catalysis , physics , nuclear physics
New photochromic surfactants, 1‐alkyl‐4‐(4′‐alkylstyryl)lpyridinium halides (C n StzRX; n = 0, 4, 6, 8; R = Me, Et, CH 2 CH 2 OH, n ‐Bu, n ‐C 9 H 19 ; X = Br, I), were synthesized and the photochemical behavior of their micellar aggregates in water was characterized in relation to non‐micellizing 1‐methyl‐4‐stilbazolium ions. Reversible trans‐cis isomerization through a photothermal cycle was observed for the micellized C n StzRX. Furthermore, photoreactions upon prolonged irradiation of C n StzRX micelles resulted in a 3–31% formation of thermodynamically least stable syn ‐head‐to‐head and ca . 3% of anti‐ head‐to‐head dimers. These findings indicate that the self aggregation process of C n StzRX may provide some topologically organized microenvironment affecting the steric and like‐charge repulsions of the aggregate components.