Visual pigments. 11. Spectroscopy and photophysics of retinoic acids and all-trans-methyl retinoate. [Photophysical properties at 77/sup 0/K]

Journal Article · Wed Apr 09 00:00:00 EST 1980 · J. Am. Chem. Soc.; (United States)

DOI:https://doi.org/10.1021/ja00528a014· OSTI ID:5129823

Takemura, T ^[1]; Chihara, K; Becker, R S; Das, P K; Hug, G L

---

1. Univ. of Houston, TX

The photophysics of hydrogen-bonded complexes of retinoic acid and its 9-cis and 13-cis isomers and the photophysics of the dimers of these isomers of retinoic acid were studied. The investigation indicated that complexes of retinoic acid and molecules that form hydrogen bonds with the carbonyl oxygen of retinoic acid (type I complexes) have both higher radiative and nonradiative rate constants than do hydrogen-bonded complexes of retinoic acid and molecules that form hydrogen bonds only with the hydroxyl oxygen of retinoic acid (type II complexes). For all-trans-retinoic acid in 3-methylpentane at 77 K, the type I complexes have radiative rate constants approximately equal to or greater than 2 x 10/sup 8/ s/sup -1/ and nonradiative rate constants greater than 3 x 10/sup 8/ s/sup -1/. Both the radiative and nonradiative rate constants of the type II complexes of all-trans-retinoic acid at 77 K in 3-methylpentane are less than 1 x 10/sup 8/ s/sup -1/. The dimer of retinoic acid (K(association) = 1 x 10/sup 4/ M/sup -1/ at room temperature for the all-trans isomer) behaves like a type I complex, and its excited-state properties are better understood in terms of hydrogen bonding than in terms of an exciton model. The photophysical properties and triplet-triplet absorption spectrum of methyl retinoate were measured. The study concluded with an examination of some of the implications of this work for the role of hydrogen bonding in the dimers and monomers of retinal and retinol.

• OSTI ID: 5129823
• Journal Information: J. Am. Chem. Soc.; (United States), Vol. 102:8
• Country of Publication: United States
• Language: English

Related Subjects

38 RADIATION CHEMISTRY, RADIOCHEMISTRY, AND NUCLEAR CHEMISTRY
37 INORGANIC
ORGANIC
PHYSICAL AND ANALYTICAL CHEMISTRY
59 BASIC BIOLOGICAL SCIENCES
ESTERS
ABSORPTION SPECTRA
EMISSION SPECTRA
INFRARED SPECTRA
PHOTOLYSIS
RADIOLYSIS
MONOCARBOXYLIC ACIDS
EXPERIMENTAL DATA
LASER RADIATION
MEV RANGE 01-10
PULSED IRRADIATION
CARBOXYLIC ACIDS
CHEMICAL RADIATION EFFECTS
CHEMICAL REACTIONS
CHEMISTRY
DATA
DECOMPOSITION
ELECTROMAGNETIC RADIATION
ENERGY RANGE
INFORMATION
IRRADIATION
MEV RANGE
NUMERICAL DATA
ORGANIC ACIDS
ORGANIC COMPOUNDS
PHOTOCHEMICAL REACTIONS
RADIATION CHEMISTRY
RADIATION EFFECTS
RADIATIONS
SPECTRA
400600* - Radiation Chemistry
400500 - Photochemistry
550200 - Biochemistry