Hybrid perylene-cored poly(amidoamine) dendrimer with coumarin and calcozine red 6G end groups: From photophysical properties to cell imaging

Abstract

In this article, we looked at how to make fluorescence hybrid dendrimers using perylenediimide (PTCDI) cores and calcozine red 6 G and coumarin end groups. Perylenetetracarboxylic dianhydride (PTCDA) is used as core, and 4th generation poly(amidoamine) dendrimer (PAMAM) is synthesized to produce PG4.0. Then, PG4.0 is reacted with calcozine red 6 G and 7-methacryloyloxy-4-methylcoumarin (MCMC). Fourier transform infrared spectroscopy (FT-IR), proton nuclear magnetic resonance (1H NMR), X-ray diffraction (XRD), and field emission scanning electron microscopy (FE-SEM) are used to characterize the structure of synthesized fluorescent hybrid dendrimers. Optical properties are demonstrated using fluorescence microscopy, a fluorescence spectrophotometer, and UV–vis–NIR reflectance spectra. Hybrid dendrimers were transparent in the NIR range, according to UV-Vis-NIR reflectance spectra. Moreover, quantum yield (Φs) of hybrid dendrimers was calculated in dimethylformamide (DMF), ethanol, and distilled water (H2O). PG4R32 and PG4M16R16 showed the maximum quantum yield in ethanol due to great interaction of structure with ethanol and the arrangement of ring-opened amide shape of calcozine red 6 G gather in compound. At long last, SH-SY5Y cells were utilized to measure cell uptake and fluorescence imaging exhibitions of PG4.0 (perylene-3,4,9,10-tetracarboxylic diimide (PTCDI)-based generation 4 amino terminated poly(amidoamine)dendrimers), PG4M32 (perylene-3,4,9,10-tetracarboxylic diimide (PTCDI)-based generation 4 amino terminated poly(amidoamine)dendrimers in which 32 amine groups of PAMAM are conjugated with coumarin derivatives), PG4R32 (perylene-3,4,9,10-tetracarboxylic diimide (PTCDI)-based generation 4 amino terminated poly(amidoamine)dendrimers in which 32 amine groups of PAMAM are conjugated with rhodamine derivatives), and PG4M16R16 (perylene-3,4,9,10-tetracarboxylic diimide (PTCDI)-based generation 4 amino terminated poly(amidoamine)dendrimers in which 16 amine groups of PAMAM are conjugated with rhodamine and coumarin derivatives) pigments, and as a result, pigments had a great capacity for live-cell fluorescence imaging.