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THE PHOTOISOMERIZATION OF RETINAL *
Author(s) -
KROPF ALLEN,
HUBBARD RUTH
Publication year - 1970
Publication title -
photochemistry and photobiology
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.818
H-Index - 131
eISSN - 1751-1097
pISSN - 0031-8655
DOI - 10.1111/j.1751-1097.1970.tb06057.x
Subject(s) - photoisomerization , isomerization , rhodopsin , retinal , photochemistry , cis–trans isomerism , chemistry , hexane , quantum yield , chromophore , stereochemistry , physics , organic chemistry , optics , catalysis , biochemistry , fluorescence
— –Quantum efficiencies have been measured for the photoisomerization of four stereoisomers of retinal ( all‐trans , 13‐ cis , 11 cis , and 9‐ cis ) in two solvents at different wavelengths of irradiation and at various temperatures. In heane at 25°C the quantum efficiencies for isomerization at 365 nm are: 9‐ cis to trans , 0.5; 13‐ cis to trans , 0.4; 11‐ cis to trans , 0.2; all‐ trans to monocis isomers, 0.2‐0.06, depending upon assumptions made regarding the stereo‐isomeric composition of the product. These values vary somewhat with the wavelength of the irradiating light. The quantum efficiency for the photoisomerization of all‐trans retinal in hexane decreases by a factor of 30 when the temperature is lowered from 25° to – 65°C; the activation energy for this photoisomerization is about 5 kcal/mole. The quantum efficiencies for the isomerization of the monocis isomers to all‐trans retinal in hexane are virtually independent of temperature. In ethanol the rates of photoisomerization from trans to cis or cis to trans depend only slightly on the temperature between 25° and – 65°C. The photosensitivities of the stereoisomers of retinal are of the same order of magnitude as those of the retinylidene chromophores of rhodopsin (11 ‐ cis ), metarhodopsin I (all‐ trans ), and isorhodopsin (9‐ cis ); but it is not yet possible to derive the photochemistry of rhodopsin uniquely and quantitatively from that of retinal.