Synthesis, solvatochromism, aggregation-induced emission and cell imaging of tetraphenylethene-containing BODIPY derivatives with large Stokes shifts

Abstract

A series of tetraphenylethene-containing BODIPYs with emissions from visible to near-IR and large Stokes shifts up to 142 nm have been designed and synthesized. They show solvatochromic fluorescence and can be utilized as fluorescent visualizers for intracellular imaging.

Twisted configuration pyrene derivative: exhibiting pure blue monomer photoluminescence and electrogenerated chemiluminescence emissions in non-aqueous media

“…Since MB-Py could be considered as a molecule with donor and acceptor constituents (see DFT computations above), the increase in the Stokes shi could be due to the intramolecular charge transfer in the excited state for the coupling of donor and acceptor. 33 In addition, the relative PL efficiencies were calculated to be 0.96 for MB-Py and 0.72 for Bz-Py, using diphenylanthracene (DPA) as a standard (l ex ¼ 431 nm, F PL ¼ 0.804 in MeCN : Bz (v/v ¼ 2 : 3)). 18 As is expected, the p-conjugation extent of the rigid features in Bz-Py is larger than that in MB-Py, which is benecial for generating more electronic excited state molecules and contributes to a higher PL efficiency.…”

Auxiliary ligand-assisted two novel one-dimensional indium coordination polymers: Synthesis, crystal structures and photoluminescence characterization effected by solvent and temperature

“…It is showed that the lifetimes of In1 and In2 at 77 K increase conspicuously to those at 298 K (298 K: τ = 4.83 μs for In1, τ = 6.18 μs for In2; 77 K: τ = 21.49 μs for In1, τ = 10.69 μs for In2) (Fig. S3), since cold conditions would be favorable to the rigidity of ligands with reducing the non-radiation decay and collisional quenching [40].…”

Photocontrolled Intramolecular Charge/Energy Transfer and Fluorescence Switching of Tetraphenylethene‐Dithienylethene‐Perylenemonoimide Triad with Donor–Bridge–Acceptor Structure

“…Instead, TPE only exhibits the electron-donating property; this conclusion contributes to a better understanding of the effect of the TPE group on the fluorescence properties and photoswitching process in solution. [15] The fluorescence emission spectrum of 1 O (Figure 1 b) is structured in toluene, and the maximum appears at 560 nm, which can be assigned to the locally excited (LE) state emission of PMI. However, with increasing solvent polarity, the emission peak exhibits a significant red shift and becomes Scheme 1.…”

“…[14] It was found in previous studies that TPE integrates the donating properties and the AIE effect. [15] To the best of our knowledge, there are few reports that TPE can act as a moderate donor when linked to strong acceptors. [15] Here, we report the synthesis and optical properties of a donor-photochromic bridge-acceptor (D-bridge-A) tetraphenylethene-dithienylethene-perylenemonoimide (TPE-DTE-PMI) triad.…”

“…[15] To the best of our knowledge, there are few reports that TPE can act as a moderate donor when linked to strong acceptors. [15] Here, we report the synthesis and optical properties of a donor-photochromic bridge-acceptor (D-bridge-A) tetraphenylethene-dithienylethene-perylenemonoimide (TPE-DTE-PMI) triad. By covalently coupling TPE and PMI using DTE, we investigate the absorption, emission, photochromism, and fluorescent photoswitching behavior of the donor-photochromic bridge-acceptor structure in solution, in aggregates, and in the solid state.…”