Fluorescence Enhancement of Bodipy by Pah via PET Annihiliation
Dikhi Firmansyah1,*, Niken Roro Hapsari1,2, Monica Christania Damanik1,2, Muhammad Yudhistira Azis2,*

1 Organic Chemistry Division, Bandung Institute of Technology, Jalan Ganesha 10, Bandung, 40132, Indonesia.
2 Analytical Chemistry Research Group, Bandung Institute of Technology, Jalan Ganesha 10, Bandung, 40132, Indonesia.
*Corresponding author, 1email: dikhfi[at]itb.ac.id, 2email: yudhistira[at]itb.ac.id

Abstract

Boron-dipyrromethene (BODIPY) is an excellent candidate for sensor and colorimetric probes due to its stability, high molar absorption coefficient, excellent fluorescence quantum yield, easy functionalization, and better compatibility for a biological system. Weak interaction of PAHs hydrogen and strained meso-aryl BODIPY is reported. In this work, we focused our study on the interaction of unstrained meso-aryl BODIPY to selected PAHs (naphthalene, phenanthrene, and anthracene). Isosbestic absorption points were obtained on PAHs addition with BODIPYs. However, fluorescence enhancement of BODIPYs by anthracene was negligible unless the alkoxy group was present. The resulting weak interaction, presumably unable to alter the rotation of meso phenyl and para-toluene BODIPY, but able to reduce PET (photoinduced electron transfer) phenomena on alkoxy-perfluorophenyl BODIPY. To our benefit, the fluorescence intensity is linear to PAH concentration. These results indicate that alkoxy-meso-aryl BODYPY could be a potential candidate for the PAH sensor through the fluorescence enhancement process.

Keywords: BODIPY- PAH- PET- Sensor- Colorimetry

Topic: Organic Synthesis and Medicinal Chemistry