Photoreduction of indigo dyes by electron donors. One- and two-electron-transfer reactions as a consequence of excited-state quenching

Journal Article · Wed May 14 00:00:00 EDT 1986 · J. Am. Chem. Soc.; (United States)

DOI:https://doi.org/10.1021/ja00270a024· OSTI ID:5454763

Schanze, K S; Lee, L Y.C.; Giannotti, C; Whitten, D G

The indigoid dyes, thioindigo (TI), N,N'-diacetylindigo, (NDI) and oxalylindigo (OI), all undergo reduction upon irradiation of the dyes in the presence of electron donors such as triethylamine (TEA) or N-benzyl-1,4-dihydronicotinamide (BNAH). Product analysis by NMR and high-resolution mass spectrometry has shown that the products for TI and NDI are the formal H/sub 2/ adducts TIH/sub 2/ and NDIH/sub 2/; the product for OI has been shown to be the semireduced radical OIH which is readily detected by its characteristic ESR spectrum. Mechanistic studies have been carried out for the visible-light-induced reduction of the three dyes.

• Research Organization: Univ. of Rochester, NY
• DOE Contract Number: AC02-84ER13151
• OSTI ID: 5454763
• Journal Information: J. Am. Chem. Soc.; (United States), Vol. 108:10
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC
ORGANIC
PHYSICAL AND ANALYTICAL CHEMISTRY
AMIDES
PHOTOCHEMICAL REACTIONS
AMINES
INDIGO
REDUCTION
ADDUCTS
ELECTRON SPIN RESONANCE
ELECTRON TRANSFER
EXCITED STATES
EXPERIMENTAL DATA
HYDROGEN
MASS SPECTROSCOPY
NMR SPECTRA
NUCLEAR MAGNETIC RESONANCE
PHOTOCHEMISTRY
RADIATIONLESS DECAY
RADICALS
AROMATICS
AZAARENES
AZOLES
CHEMICAL REACTIONS
CHEMISTRY
DATA
DE-EXCITATION
DYES
ELEMENTS
ENERGY LEVELS
ENERGY TRANSFER
ENERGY-LEVEL TRANSITIONS
HETEROCYCLIC COMPOUNDS
INDOLES
INFORMATION
MAGNETIC RESONANCE
NONMETALS
NUMERICAL DATA
ORGANIC COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
PYRROLES
RESONANCE
SPECTRA
SPECTROSCOPY
400500* - Photochemistry
400301 - Organic Chemistry- Chemical & Physicochemical Properties- (-1987)