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An unexpected dual-emissive luminogen with tunable aggregation-induced emission and enhanced chiroptical property

ABSTRACT: In the literature, organic materials with both aggregation-induced emission (AIE) and aggregation-caused quenching (ACQ) effects that can emit with multiple bands both in the solution and aggregated state are rarely reported. Herein we report a novel chiral dual-emissive bismacrocycle with tunable aggregation-induced emission colors. A facile four-step synthesis strategy is developed to construct this rigid bismacrocycle, (1,4)[8]cycloparaphenylenophane (SCPP[8]), which possesses a 1,2,4,5-tetraphenylbenzene core locked by two intersecting polyphenylene-based macrocycles. The luminescent behavior of SCPP[8] shows the unique characteristics of both ACQ effect and AIE effect, inducing remarkable redshift emission with near white-light emission. SCPP[8] is configurationally stable and possesses a novel shape-persistent bismacrocycle scaffold with a high strain energy. In addition, SCPP[8] displays enhanced circularly polarized luminescence properties due to AIE effect. Organic materials with both aggregation induced emission (AIE) and aggregation-caused quenching (ACQ) effects that can emit with multiple wavelengths in the solution and aggregated state are rarely reported. Here, the authors report a chiral dual-emissive bismacrocycle which shows the unique ACQ and AIE effects inducing redshift emission with near white-light emission.

SUBMITTER: Zhang X

PROVIDER: S-EPMC9213505 | biostudies-literature | 2022 Jan

REPOSITORIES: biostudies-literature

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Project description:Positional isomers of zinc-nitrobenzoate complexes possessing pyridine -3-(or-4-) carboxamide are used for a comparative theoretical and experimental study to understand their utility as model complexes to understand the role of metal-to-ligand charge transfer in aggregation-induced emission (AIE). Among the five different model zinc complexes, four of them are non-ionic, and one is an ionic complex. The frontier molecular energy levels of different combinations of the positional isomeric complexes and the absorption maximum were ascertained by density functional theory calculations. The PolyQ value obtained from solid samples of each complex is different. Shifts in the emissions to higher wavelengths than the expected emission for the S1 to S0 transition were observed due to aggregations. The highest value of PolyQ among the complexes was 13.56% observed for emission at 439 nm (λex = 350) of the non-ionic complex, namely, (di-aqua)bis(pyridine-3-carboxamide)di(2-nitrobenzoato)zinc(II) monohydrate. Close resemblance in emission lifetime decay profiles of the solid samples of those complexes and the respective solutions of those complexes in dimethyl sulfoxide with or without water showed a common trend, suggesting aggregation-induced emission in each case. Aggregation-induced emission caused by adding water in dimethyl sulfoxide solution of each complex showed an initial increase without a shift in the emission wavelength followed by a quenching with a shift of the respective emission peak to a short wavelength. Dynamic light scattering studies showed an increase in the average particle sizes upon an increase in the concentration of water. This indicated initial participation of water molecules to form aggregates with the complexes, favoring an increase in the AIE intensity. Aggregation of each complex changes with the concentration of water, and an increase in the concentration of water beyond a characteristic limit causes lowering of the emission intensity to the short wavelength.

Project description:Photodynamic therapy (PDT) has been widely applied in the clinic for the treatment of various types of cancer due to its precise controllability, minimally invasive approach and high spatiotemporal accuracy as compared with conventional chemotherapy. However, the porphyrin-based photosensitizers (PSs) used in clinics generally suffer from aggregation-caused reductions in the generation of reactive oxygen species (ROS) and limited tissue penetration because of visible light activation, which greatly hampers their applications for the treatment of deep-seated tumors. Methods: We present a facile strategy for constructing a NIR-regulated cancer theranostic nanoplatform by encapsulating upconversion nanoparticles (UCNPs) and a luminogen (2-(2,6-bis((E)-4-(phenyl(40-(1,2,2-triphenylvinyl)-[1,10-biphenyl]-4-yl)amino)styryl)-4H-pyran-4-ylidene)malononitrile, TTD) with aggregation-induced emission (AIEgen) characteristics using an amphiphilic polymer, and further conjugating cyclic arginine-glycine-aspartic acid (cRGD) peptide to yield UCNP@TTD-cRGD NPs. We then evaluated the bioimaging and anti-tumor capability of the UCNP@TTD-cRGD NPs under NIR light illumination in an in vitro three-dimensional (3D) cancer spheroid and in a murine tumor model, respectively. Results: With a close match between the UCNP emission and absorption of the AIEgen, the synthesized NPs could efficiently generate ROS, even under excitation through thick tissues. The NIR-regulated UCNP@TTD-cRGD NPs that were developed could selectively light up the targeted cancer cells and significantly inhibit tumor growth during the NIR-regulated PDT treatment as compared with the cells under white light excitation. Conclusion: In summary, the synthesized UCNP@TTD-cRGD NPs showed great potential in NIR light-regulated photodynamic therapy of deep-seated tumors. Our study will inspire further exploration of novel theranostic nanoplatforms that combine UCNPs and various AIEgen PSs for the advancement of deep-seated tumor treatments with potential clinical translations.

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An unexpected dual-emissive luminogen with tunable aggregation-induced emission and enhanced chiroptical property

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