Kinetics of singlet oxygen sensing using 9-substituted anthracene derivatives#.

Sasikumar, Devika; Kohara, Reiko; Takano, Yuta; Yuyama, Ken-ichi; Biju, Vasudevanpillai

Abstract: Singlet oxygen (1O2), the lowest excited-state of molecular oxygen receives great attention in basic research and clinical and industrial settings. Despite several spectroscopic methods available for 1O2 sensing, fluorescence sensing receives great attention, for which many fluorogenic sensors based on substituted anthracene are reported. Nonetheless, the roles of substituents on the sensing efficiency, in terms of detection time, remain largely unknown. In this work, we examine the 1O2 sensing efficiency of a fluorescence sensor based on a coumarin-anthracene conjugate, which is an electron donor-acceptor dyad, and compare the efficiency with that of 9-methylanthracene. Here, 1O2 is generated using the standard photosensitizer Rose Bengal, which is followed by estimation of the rate of reaction of 1O2 to the sensor and 9-methylanthracene. The second order reaction rate of the sensor is an order of magnitude less than that of 9-methylanthracene. The lower reactivity of the sensor to 1O2 suggests that the roles of substituents, such as electronic interactions, steric interactions and the reactivity of precursor complexes, on sensing efficiency should be carefully considered during construction of fluorogenic molecular sensors.Graphical Abstract: SYNOPSIS The kinetics of singlet oxygen sensing using a 9-substituted anthracene derivative is studied by comparing the photooxidation rates of a conjugate between 9-methyl anthracene and a coumarin dye. The singlet oxygen sensing rate points out that the electronic interaction and steric effect induced by the substituents on anthracene influence the kinetics of sensing.

ANTHRACENE derivatives; REACTIVE oxygen species; ANALYTICAL mechanics; FLUORESCENCE; ANTHRACENE

Journal of Chemical Sciences, 2019, Vol 131, Issue 1, p1

0974-3626

Academic Journal

10.1007/s12039-018-1578-1