BODIPY‐Based Oligo(ethylene glycol) Dendrons as Fluorescence Thermometers: When Thermoresponsiveness Meets Intramolecular Electron/Charge Transfer

Abstract

The temperature-dependent photophysical properties of a series of 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) derivatives with different oligo(ethylene glycol) (OEG) dendrons were investigated. Weak fluorescence emission was observed for these BODIPY derivatives in dilute solution with low viscosity. BDP-G0 and BDP-G1-TEG exhibit a high quantum yield in viscous glycerol solutions, contrary to the moderate and little fluorescence enhancement for BDP-G1 and BDP-G2 under the same conditions. The photoinduced electron transfer (PET) may have quenched the fluorescence, as supported by calculation. Interestingly, the thermoresponsive BODIPY derivatives show heat-induced luminescence enhancement with a high signal-to-noise ratio and their emission maxima are dependent on the structures of branched tri(ethylene glycol) moieties. Finally, preliminary studies on the BODIPY derivatives as intracellular fluorescence indicators in living HeLa cells were carried out.

Near‐Infrared‐Emissive Amphiphilic BODIPY Assemblies Manipulated by Charge‐Transfer Interaction: From Nanofibers to Nanorods and Nanodisks

“…The emission band of BBDP was located in the NIR range on account of the extensive conjugated pyrene–BODIPY architecture. Besides, BBDP showed small Stokes shifts in various solvents (less than Δ λ =30 nm), which indicated that there were weak intramolecular donor–acceptor interactions in the ground state . More information about the photophysical data of BBDP are summarized in Table S1 (Supporting Information).…”

“…Formyl-modified OEG dendrons 1 followed ac lassic synthetic pathway to BODIPY derivatives to afford target molecule 2. [45] Then, compound 2 underwent aK noevenagel reactionw ith 1-pyrenecarboxaldehydet og enerate the final BBDP product. [26] PBI and MV were obtained according to the literature.…”

“…2:C ompound 1 was synthesized according to the literature. [45] Compound 1 (700 mg, 0.97 mmol) and 2-methylpyrrole (162 mg, 2.0 mmol) were dissolved in anhydrous CH 2 Cl 2 (150 mL). Trifluoroacetic acid (TFA, 2drops) was added to the mixture as the catalyst.…”

Imine‐linked porous organic polymers showing mesoporous microspheres architectures with tunable surface roughness

“…For example, the luminescent POPs with tunable surface morphologies have rarely been referred. We have been interested in fluorescent amphiphilic 4,4‐difluoro‐4‐bora‐3a,4a‐diaza‐s‐indacene (BDP) derivatives since 2014 . Very recently, a novel about dimeric BDP molecules based POPs could be realized by using FeCl 3 at room temperature was reported .…”

A PEGylated colorimetric and turn-on fluorescent sensor based on BODIPY for Hg(ii) detection in water

“…[28][29][30][31] For example, the styryl-substituted BODIPY could effectively induce a red shift of the absorption and emission maxima. 45 The water-soluble BODIPY chemosensors have also received much attention, which could be achieved by introducing some hydrophilic moieties such as oligo-(ethyleneglycol) chains, [46][47][48][49][50] sulfonates, 51-53 phosphonates 54 and zwitterionic sulfobetaines. 32 However, for most of the small molecular Hg 2+ chemosensors, their water solubility is very limited, since these chemosensors are hydrophobic and have big rigid conjugated planes inducing aggregation between them.…”