Hydrophilic, Red-Emitting, and Thermally Activated Delayed Fluorescence Emitter for Time-Resolved Luminescence Imaging by Mitochondrion-Induced Aggregation in Living Cells.

Thermally activated delayed fluorescence (TADF) materials have provided new strategies for time-resolved luminescence imaging (TRLI); however, the development of hydrophilic TADF luminophores for specific imaging in cells remains a substantial challenge. In this study, a mitochondria-induced aggregation strategy for TRLI is proposed with the design and utilization of the hydrophilic TADF luminophore ((10-(1,3-dioxo-2-phenyl-2,3-dihydro-1H-benzo[de]isoquinolin-6-yl)-9,9-dimethyl-9,10-dihydroacridin-2-yl)methyl)triphenylphosphonium bromide (NID-TPP). Using a nonconjugated linker to introduce a triphenylphosphonium (TPP+) group into the 6-(9,9-dimethylacridin-10(9H)-yl)-2-phenyl-1H-benzo[de]isoquinoline-1,3(2H)-dione (NID) TADF luminophore preserves the TADF emission of NID-TPP. NID-TPP shows clear aggregation-induced delayed fluorescence enhancement behavior, which provides a practical strategy for long-lived delayed fluorescence emission in an oxygen-containing environment. Finally, the designed mitochondrion-targeting TPP+ group in NID-TPP induces the adequate accumulation of NID-TPP and results in the first reported TADF-based time-resolved luminescence imaging and two-photon imaging of mitochondria in living cells.

Zn(2+)-cyclen-based complex enable a selective detection of single-stranded thymine-rich DNA in aqueous buffer.

It is a big challenge to develop fluorescent probes for selective detection of DNA with specific sequences in aqueous buffers. We report a new tetraphenylethene-based Zn(2+)-cyclen complex (TPECyZn), and a chemo-sensing ensemble of the Zn complex with phenol red. TPECyZn showed significant fluorescence enhancement upon binding to thymine-rich DNA in HEPES buffers. But its selectivity was not high enough to eliminate the interference from some random DNA. By constructing the chemo-sensing ensemble of TPECyZn with phenol red, the background fluorescence was eliminated due to the energy transfer from TPECyZn to phenol red. Moreover, this chemo-sensing ensemble revealed high selectivity in detecting thymine-rich single-stranded DNA over other DNA in aqueous buffer. It can detect poly deoxythymidylic acid sequence as short as 2 nt. This detection in aqueous media makes this probe feasible in real application.

Amino-modified tetraphenylethene derivatives as nucleic acid stain: relationship between the structure and sensitivity.

A series of new amino-functionalized tetraphenylethene (TPE) derivatives were designed and synthesized to study the effect of molecular structures on the detection of nucleic acid. Contrastive studies revealed that the number of binding groups, the length of hydrophobic linking arm and the configuration of TPE molecule all play important roles on the sensitivity of the probes in nucleic acid detection. Z-TPE3 with two binding amino groups, long linking arms, and cis configuration was found to be the most sensitive dye in both solution and gel matrix. Z-TPE3 is able to stain dsDNA with the lowest amount of 1 ng and exclusively stain 40 ng of short oligonucleotide with only 10 nt. This work is of important significance for the further design of TPE probes as biosensors with higher sensitivity.