Photophysical characterization and fluorescence cell imaging applications of 4-N-substituted benzothiadiazoles

Abstract

Herein we report the structure–photophysical relationship and cell imaging utility of a series of N-substituted benzothiadiazoles.

Sensitive hydrazine detection and quantification with a fluorescent benzothiadiazole sensor: selective lipid droplets andin vivoimaging

“…This behavior is similar to the fluorescent BTDs previously reported by us 108 and by others. 77,80 Given the lipophilic character of the chemical sensor (BTD-CHO), the bioprobe was subjected to the SDS test 64,90,104,107,113 to verify the light-up effect in lipophilic media (Fig. S4 †), as a prelude to the cellular behavior.…”

“…2,1,3-Benzothiadiazole (BTD) fluorescent markers are a new class of bioprobes that have been successfully applied in bioimaging experiments, as we reviewed elsewhere. 61,62 Several groups 63–94 have effectively applied new fluorescent BTD derivatives as bioimaging probes to study different biological features. Although desirable physicochemical features, photoproperties, and stabilities are typically noted for fluorescent BTD derivatives, 95–100 to the best of our knowledge, no fluorogenic BTD has been applied as a sensitive and selective sensor for hydrazine detection, especially in live cells and multicellular models ( in vivo applications).…”

An Indolin‐3‐imine Photobase and pH Sensitive Fluorophore

“…The synthesis and full characterization of Ind has previously been described in detail in the Supporting Information of our preceding paper. [17] NMR Spectroscopy NMR spectra were recorded at 298 K using an Agilent MR400-DD2 instrument at 400 MHz ( 1 H) and 101 MHz ( 13 C) or a Bruker Avance Neo instrument at 500 MHz ( 1 H) and 126 MHz ( 13 C). Chemical shifts (δ) are reported in ppm using the residual solvent peak in DMSO-d 6 (δ H = 2.50 and δ C = 39.52 ppm) as internal reference.…”

“…The Stokes shifts are quite large (52-90 nm, 3.4-3.8×10 3 cm À 1 ) and the fluorescence quantum yields (Φ F ) range from 0.03-0.15, with the lowest value obtained from measurements in toluene. Importantly, and in the light of our recent publication of the photolabile ketone analogue of Ind, [17] it should be emphasized that Ind features high photostability (ESI, Figure S7).…”

Access to long-lived room temperature phosphorescence through auration of 2,1,3-benzothiadiazole

“…As part of our ongoing research into harnessing the photophysical properties of BTD derivatives, [19][20][21][22] we sought to investigate BTD-Au(I) complexes as promising luminophores. Here, we report a series of emissive aryl-Au(I)-L complexes in which the gold centre is directly attached to the highly electron-deficient 2,1,3-benzothiadiazole (BTD) unit via a C-Au bond (Scheme 1).…”