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2,7‐DIIODO‐9‐DIAZOFLUORENE: A POTENTIAL REAGENT FOR PHOTOLABELING
Author(s) -
Rak Stanton F.,
Schuster Gary B.
Publication year - 1987
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.1751-1097.1987.tb05400.x
Subject(s) - carbene , diazo , chemistry , electrophile , photochemistry , triplet state , singlet state , reagent , ground state , ultrafast laser spectroscopy , spectroscopy , organic chemistry , molecule , excited state , atomic physics , catalysis , physics , quantum mechanics
— The photochemistry of 2,7‐diiodo‐9‐diazofiuorene was studied to examine its suitability as a photolabeling agent of hydrophobic sites in biological assemblies. Irradiation of the diazo compound generates 2,7‐diiodofluorenylidene. The carbene was detected by laser transient absorption spectroscopy and characterized by its chemical and physical properties. Like fluorenylidene, the triplet is the ground state of 2,7‐diiodofluorenylidene. However, the substituted triplet carbene does not reform its higher energy, electrophilic singlet state fast enough for reactions of the upper state to compete with the irreversible consumption of the triplet. Thus, the products from the reactions of diiodofluorenylidene contain a higher proportion of those characteristic of the triplet carbene than occurs in the reactions of fluorenylidene. This will limit the utility of this diazocompound as a photolabeling agent.