Chemiluminescence From the Thermal Decomposition of 1,4-Diphenyl-1,4-Dioxa-2-Benzopyran-3-One. Direct and Indirect Luminescence Involving an Ortho-Xylylene Peroxide

1,4-Dipheny1-1,4-dioxa-2-benzopyran-3-one (37), an endoperoxide similar in structure to the endoperoxide proposed as an intermediate in the chemiluminescent reaction of luminol, is prepared by the addition of singlet oxygen to 1,4-diphenyl-2-benzopyran-3-one. This endoperoxide yields o-dibenzoyl-benzene and phenyl-(o-benzoyl) benzoate upon thermolysis in p-xylene at 112(DEGREES)C. Chemiluminescence is observed during the decomposition of the endoperoxide. Light is also produced when 37 is heated to 112(DEGREES)C in the presence of added fluorescers. The direct chemiluminescence is the result of electron-transfer (CIEEL) between two intermediates formed during the thermolysis of 37. One intermediate has been identified as 1,4-diphenyl-2,3-benzodioxin, the first of a new class of compounds we call o-xylylene peroxides. The other intermediate remains unidentified. The chemiluminescence in the presence of fluorescers is explained by the CIEEL mechanism with the fluorescer and the o-xylylene peroxide as the reactive species.

Name thesis:degree_name

Ph.D.

Level thesis:degree_level

Dissertation

Discipline thesis:degree_discipline

Chemistry

Grantor

University of Illinois at Urbana-Champaign

Year dc:date

2014

Author dc:creator

• Smith, Jimmie Prince

• Chemistry, Organic

Language dc:language

eng

Identifier

(UMI)AAI8127694

OAI identifier oai:identifier

oai:www.ideals.illinois.edu:2142/67284