Effects of substituents on the optical properties of AIEE-active 9, 10-dithiopheneanthrylene derivatives and their applications in cell imaging

Multiresponsive tetrarylethylene-based fluorescent dye with multicoloreded changes: AIEE properties, acidichromism, Al3+ recognition, and applications

“…Organic fluorescent materials have attracted wide attention in photoelectric devices, biosensing, fluorescence switches, pH, and ion sensors due to their highly variable structure, flexible molecular preparation methods, diversity of fluorescent colors, high sensitivity, and excellent physical and chemical properties. [1][2][3][4][5] Nevertheless, the development and application of fluorescent devices have been limited by traditional fluorescent groups, which have strong aggregation-caused quenching (ACQ) effects and are almost completely quenched in the molecular aggregation or solid states. 6,7 Fortunately, Tang et al reported a 1-methyl-1,2,3,4,5-pentaphenylsilole compound, which exhibited strong fluorescence emission in solid and aggregated states, and then aggregation-induced emission (AIE) was proposed.…”

AIEE compounds based on 9,10-dithienylanthracene-substituted triphenylamine: design, synthesis, and applications in cell imaging

“…Firstly, 5-(10-(5-bromothiophene-2-yl)anthracene-9-yl)thiophene-2-carbaldehyde ( 1 ) was synthesized from 5-(9-bromoanthracene-10-yl)thiophene-2-carbaldehyde and (5-bromothiophene-2-yl)boronic acid according to the reported method. 49 Then, 5-(10-(5-(triphenylamine)thiophene-2-yl)anthracene-9-yl)thiophene-2-carbaldehyde ( TPA-DTA-C ) was prepared through Suzuki coupling of compound 1 with 4-(diphenylamino)phenylboronic acid. Finally, compound TPA-DTA-C was coupled with phenylacetonitrile derivatives to give 5-(10-(5-(triphenylamine)thiophene-2-yl)anthracene-9-yl)thiophene-2-( p -(methoxy)phenyl)acrylonitrile ( TPA-DTA-PAM ), 5-(10-(5-(triphenylamine)thiophene-2-yl)anthracene-9-yl)thiophene-2-( p -(trifluoromethyl)phenyl)acrylonitrile ( TPA-DTA-PATF ) and 5-(10-(5-(triphenylamine)thiophene-2-yl)anthracene-9-yl)thiophene-2-phenylacrylonitrile ( TPA-DTA-PA ) through the Knoevenagel condensation reaction, respectively.…”

“…41–46 Currently, most of the anthracene-based compounds with AIE behaviors are DSA, while other anthracene-based AIE materials are rarely reported. In previous work, we found that 9,10-dithienylanthracene ( DTA ) has similar AIE properties to DSA, 47–49 but its emission wavelength is not very long, so it is very desired to synthesize DTA derivatives with longer wavelength emission. In general, organic fluorescent molecules containing electron donors and acceptors are beneficial for forming a push–pull “D–π–A” electronic system, which can separate the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO), leading to red-shifted emission.…”

A difluoroboron compound with latent fingerprint detection and inkless writing based on aggregation-induced emission enhancement and mechanofluorochromic behavior

“…When f w was beyond 60%, the solvating power of the solvent matters more than the polarity, the restricted intramolecular rotation induced the dissociative molecules of TPA-Py-Br BF 2 to form aggregates. 30 In the aggregate state, the nonradiative transition process was suppressed, showing that the emission was dramatically increased. As f w reached 80%, the emission peak was blue-shifted to 545 nm with yellow light and the emission intensity reached maximum, as shown in Fig.…”

“…S6 (ESI †), TPA-Py-Br BF 2 was selfassembled and formed rod-like nano-aggregates ( f w = 80%), demonstrating that the self-assembly brought about tightly packed aggregation. These small particle size and strong emission of TPA-Py-Br BF 2 aggregations could provide a facile route to acquiring nanoscale AIEE-active fluorescent dyes, 30,33 which was instrumental in latent fingerprint detection applications.…”