10,15-Bis(ethoxycarbonyl)-5-(4-methoxycarbonylphenyl) B(III)subchlorin: A photosensitizer with high singlet oxygen producing efficiency

Abstract

A novel A2B-type B(III)subchlorin has been synthesized for the first time in two ways possessing two different ester moieties upon macrocyclic periphery from meso-diethoxycarbonyl tripyrrane. Its photophysical and electrochemical properties have been explored. Introduction of the third meso-substituent resulted in the synthesis of the B(III)subchlorin as the major product with the formation of minor oxidized B(III)subporphyrin analogue. This subchlorin derivative was found to generate singlet oxygen much efficiently with quantum yield ([Formula: see text] 0.88.

The p-Metal Porphyrins: from Specificity of Properties to Application in Medicine, Catalysis, and Optoelectronics

“…[56] The subchlorin derivative, 10,15-bis(ethoxycarbonyl)-5-(4-methoxycarbonylphenyl)B(III)subchlorin, generates singlet oxygen with quantum yield (F D ) 0.88. [93] Attempts are being made to control the properties of these compounds to increase of their application efficiency. More economical synthesis of highly desirable compounds such as TOOKAD (palladium bacteriopheophorbide) and other (metallo)bacteriopyropheophorbides consisting in the use of microwave heating metallation method was discovers for the obtaining of tin and indium bacteriopyropheophorbides.…”

Synthesis of Trifluoromethyl-Substituted [14]Triphyrin(2.1.1), Its Selective Reduction to Triphachlorin, and Stable Isomeric Triphabacteriochlorins via Direct Detrifluoromethylation

“…These molecules are endowed with a 14π-aromatic electronic circuit having bowl-shaped geometry owing to B­(III) coordination in a tetrahedral fashion. Despite their interesting photophysical properties, there has been no further development in their chemistry until our recent report, which established a simple synthetic route to subchlorin upon introduction of the electron-withdrawing ethoxycarbonyl moieties at its two meso positions and demonstrated their use in PDT . Swapping the ester moieties with a strong electron-withdrawing CF 3 group also resulted in only B­(III)­subchlorin, albeit in a trace amount because of the hydrolysis of the trifluoromethyl units under the reaction conditions .…”