The design, synthesis, and photophysical properties of new fluorene based aza-boron-dipyromethethene (aza-BODIPY) dyes featuring pendant diphenylamino fluorene substituents were successfully achieved. Recent studies have shown that it is possible to red-shift the photophysical properties of the aza-BODIPY by the addition of an amino group. The fluorene moiety increases conjugation allowing further increase of the absorption into the red near-infrared (NIR) region. The longest wavelength peak maxima in the linear absorption spectrum for probes 1  and 2  were 768 and 648 nm, while the 2PA cross sections were 700 and 530 GM at 1140 and 1020 nm, respectively. The neutral dyes were essentially nonfluorescent while protonation turned on the fluorescence, with emission in the NIR. Successful titrations of our probes with acids indicate that these could serve as potential turn on pH probes, namely in biological samples. Probes 1  and 2  were successfully encased in Pluronics and incubated in HCT116 cells. Two-photon fluorescent microscopy (2PFM) cell images will also be reported.

Nonlinear optical characterization, pH titration and 2PFM imaging of novel near–infrared diphenylaminofluorene-based aza-BODIPY dyes

245th National Meeting (2013)

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