Development of highly efficient circularly polarized organic light‐emitting diodes (CPOLEDs) has gained increasing interest as they show improved luminous efficiency and high contract 3D images in OLED displays. In this work, a series of binaphthalene‐containing luminogenic enantiomers with aggregation‐induced emission (AIE) and delayed fluorescence properties is designed and synthesized. These molecules can emit from green to red light depending on the solvent polarity due to the twisted intramolecular charge transfer effect. However, their solid powders show bright light emissions, demonstrating a phenomenon of AIE. All the molecules exhibit Cotton effects and circularly polarized luminescence in toluene solution and films. Multilayer CPOLEDs using the doped and neat films of the molecules as emitting layers are fabricated, which exhibit high external quantum efficiency of up to 9.3% and 3.5% and electroluminescence dissymmetry factor (gEL) of up to +0.026/−0.021 and +0.06/−0.06, respectively. Compared with doped CPOLEDs, the nondoped ones show higher gEL and much smaller current efficiency roll‐off due to the stronger AIE effect. By altering the donor unit, the electroluminescence maximum of the doped film can vary from 493 to 571 nm. As far as it is known, this is the first example of efficient CPOLEDs based on small chiral organic molecules.
Photodynamic therapy
(PDT) is a promising noninvasive therapeutic
technique and has attracted increasing interests in preclinical trials.
However, the translation from laboratory to clinic often encounters
the problem of undesired dark cytotoxicity of photosensitizers (PSs).
Now, this challenge can be addressed by cascaded substitution activated
phototheranostics using the host–guest strategy. Through electrostatical
complexation of pyridinium-functionalized tetraphenylethylene, namely,
TPE-PHO, and water-soluble calixarene, the dark cytotoxicity of TPE-PHO
is dramatically inhibited. The nanoassemblies of the complex show
enhanced biocompatibility and selectively locate at the cytoplasm
in vitro. When TPE-PHO is competitively displaced from the cavity
of calixarene by 4,4′-benzidine dihydrochloride at the tumor
site, its dark cytotoxicity and photoactivity in tumor tissue are
restored to give efficient PDT efficacy under light irradiation. The
result from cell imaging reveals that TPE-PHO undergoes translocation
from cytoplasm to mitochondria to kill the cancer cells during the
cascaded supramolecular substitution process. In vivo tumor imaging
and therapy are successfully implemented to evaluate the curative
effect. Such a supramolecular strategy avoids tedious molecular synthesis
and opens a new venue to readily tune the PS behaviors.
This article presents a new strategy to achieve white-light emission from single tetraphenylethylene-substituted pyrenes (TPE-Pys) with aggregation-induced emission (AIE) characteristics.
There is a great demand to understand cell transplantation, migration, division, fusion, and lysis. Correspondingly, illuminant object-labeled bioprobes have been employed as long-term cellular tracers, which could provide valuable insights into detecting these biological processes. In this work, we designed and synthesized a fluorescent polymer, which was comprised of hydrophilic N-isopropylacrylamide polymers as matrix and a hydrophobic tetraphenylethene (TPE) unit as AIE-active cross-linkers (DDBV). It was found that when the feed molar ratio of N-isopropylacrylamides to cross-linkers was 22:1, the produced polymers demonstrated the desirable LCST at 37.5 °C. And also, the temperature sensitivity of polymers could induce phase transfer within a narrow window (32-38 °C). Meanwhile, phase transfer was able to lead the florescent response. And thus, we concluded that two responses occur when one stimulus is input. Therefore, the new cross-linker of DDBV rendered a new performance from PNIPAm and a new chance to create new materials. Moreover, the resulted polymers demonstrated very good biocompatibility with living A549 human lung adenocarcinoma cells and L929 mouse fibroblast cells, respectively. Both of these cells retained very active viabilities in the concentration range of 7.8-125 μL/mg of polymers. Notably, P[(NIPAm)22-(DDBV)1] (P6) could be readily internalized by living cells with a noninvasive manner. The cellular staining by the fluorescent polymer is so indelible that it enables cell tracing for at least 10 passages.
Development of efficient polymerizations is crucial for polymer science from which polymeric materials with versatile properties could be produced. In this work, a new and efficient spontaneous amino-yne click polymerization is successfully established by using activated diynes of bis(ethynylsulfone)s. Compared with the ester-activated diynes, that is, dipropiolates, bis(ethynylsulfone)s could polymerize with all kinds of diamines including aliphatic and aromatic primary and secondary ones under very mild reaction conditions, and soluble and thermally stable poly(β-aminovinylsulfone)s (PAVSs) with high weightaverage molecular weights (M w up to 160,000) and excellent regio-and stereoregularity (the ratio of E isomers up to 100%) were obtained in high yields (up to 99%). Due to the strong electron-withdrawing ability of sulfonyl groups, the resultant PAVSs show a dynamic property and could undergo the amine exchange, which makes the polymers readily degrade upon addition of monoamines. Moreover, this highly efficient spontaneous amino-yne click reaction could be used to facilely label and decorate proteins. Thus, this work not only establishes a more efficient amino-yne click polymerization, which could be used to label bioconjugates, but also provides a novel strategy to construct regio-and stereoregular dynamic polymers.
Non-doped organic light-emitting diodes (OLEDs) using pyrene-based AIE luminogens as emitters displayed sky-blue light at 492 nm at a low turn-on voltage (3.1 V) with a maximum luminance of 15 750 cd m−2 and a current efficiency of 7.34 cd A−1 with a low efficiency roll-off.
Multicomponent polymerizations (MCPs) as a burgeoning field in polymer chemistry has proved to be a powerful and popular tool for the synthesis of functional polymer materials with diverse and complex structures. To explore the general applicability of MCPs and enrich the product structures of MCPs, multicomponent tandem polymerizations (MCTPs) with great synthetic simplicity and efficiency were pursued. In this work, MCTPs of N-(2iodophenyl)-3-phenyl-N-tosylpropiolamide, aromatic terminal alkynes, and diamines were explored through combining Sonogashira coupling and Michael addition reaction in a one-pot procedure. The MCTPs could proceed efficiently and conveniently under mild conditions with Pd(PPh 3 ) 2 Cl 2 , CuI, and i-Pr 2 NEt, affording 12 poly(indolone)s with unique structures and high M w s (up to 30400 g/mol) in high yields (up to 97%). The poly(indolone)s possess a unique acid-triggered fluorescence "turn-on" response which could realize specific detection of CF 3 SO 3 H from other inorganic and organic acids through a rapid acid-catalyzed reaction from enamine to ketone.
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