Triangular Triazine-Triphenylamine Functionalized Hybrid Fluorescent Porous Polymers for Detection and Photodegradation of Tetracycline Hydrochloride.

ABSTRACT

First, an organic semiconductor fluorescent molecule of 4',4″,4"'-(2,4,6-triphenyl-1,3,5-triazine)-4-(N,N-diphenyl-(1,1'-biphenyl)-4-amine (TPTz) is successfully synthesized by the Suzuki-Miyaura coupling reaction of 2,4,6-tris(4-bromophenyl)-1,3,5-triazine with 4-(diphenylamino)phenylboronic acid. TPTz offers as high as 85% fluorescence quantum yield and a strong solvent effect, with fluorescent colors across the visible spectrum in different solvents. Then, an organic-inorganic hybrid fluorescent porous polymer of PCS-TPTz with a surface area of 714 m2 g-1 and pore volume of 0.660 cm3 g-1 is prepared by the Friedel-Crafts reaction of TPTz and octavinylsilsesquioxane; PCS-TPTz showed a high fluorescence quantum yield of 17% with a large Stokes shift of up to 280 nm. The excellent fluorescence properties and insolubility of PCS-TPTz make it to act as a heterophase sensor for tetracycline hydrochloride (TH) with a KSV of 2.39 × 104 M-1. In addition, PCS-TPTz exhibits an excellent photodegradation activity for antibiotic TH without the requirement for additional oxidants or pH adjustments. ESR spectra and free radical trapping experiment indicate that superoxide radical (•O2-) is the active radical for achieving the photodegradation. The simultaneous detection and degradation of TH are achieved by PCS-TPTz.