102699-15-0Relevant articles and documents
Chemiluminescence Mechanism and Quantum Yield of Synthetic Vinylpyrene Analogues of Benzopyrene-7,8-dihydrodiol
Thompson, Ambler,Lever, John R.,Canella, Karen A.,Miura, Kyo,Posner, Gary H.,Seliger, H. H.
, p. 4498 - 4504 (1986)
We have previously reported that the dioxetane chemiluminescence (CL) of the proximate carcinogenic metabolite (+/-)-trans-7,8-dihydroxy-7,8-dihydrobenzopyrene (7,8-Diol) could be produced by free singlet oxygen (1O2) in solution.We now report that the trans-1-(2-methoxyvinyl)pyrene (t-MVP) model chemical analogue, in which an ene reaction is prevented, has a CL quantum yield ΦCL (t-MVP) of 0.0003, 180 times that of 7,8-diol.The CL emission spectrum of t-MVP was identical with the fluorescence emission spectrum of the dioxetane decomposition product, pyrene-1-carboxaldehyde (6 in Scheme II), which was isolated in 10 percent yield in 1O2 reactions.The solvent dependencies of ΦCL t-MVP of dioxetanes parallel the fluorescence quantum yield (ΦFluor) of 6 and the CL yield from dioxetanes of 7,8-Diol in these same solvents.This dioxetane CL of the t-MVP analogue supports the originally proposed dioxetane CL mechanism of 7,8-Diol.The limiting factor in 7,8-Diol CL appears to be the low chemical yield for formation of the 9,10-dioxetane.
