Catalytic Chiral Photochemistry Sensitized by Chiral Hosts-Grafted Upconverted Nanoparticles

Rao, Ming; Fan, Chunying; Ji, Jiecheng; Liang, Wenting; Wei, Lingling; Zhang, Dongjing; Yan, Zhiqiang; Wu, Wanhua; Yang, Cheng

doi:10.1021/acsami.2c02313

Cited by 13 publications

(9 citation statements)

References 59 publications

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“…It is worth noting that modifying the host and altering external factors are viable strategies to enhance the stereoselectivity of chiral photoreactions. The discourse commences with the effect of the structural characteristics of cyclodextrins and essential observations on how external factors influence the stereochemical consequences of enantiodifferentiating photocyclodimerization of anthracene derivatives. ,,, More complicated supramolecular chiral environments, including rotaxanes, CD–pillar[5]arene-hybridized host, metal nanohelices, and CD-modified upconverted nanoparticles (UCNP), , have also been constructed and exhibited unique supramolecular photochirogenesis behaviors. Moreover, intelligent molecular chiroptical photoswitches capable of performing complex functions have been constructed based on photoinduced isomerization. , …”

Section: Introductionmentioning

confidence: 99%

Asymmetric Photoreactions in Supramolecular Assemblies

Wei

et al. 2023

Acc. Chem. Res.

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Metrics & MoreArticle Recommendations CONSPECTUS: Stereochemical control of excited-state asymmetric photoreactions has been one of the most challenging topics of modern photochemistry. The short-lived character of electronically excited photosubstrates and their low activation energy barriers to form both enantiomers are the major obstacles to achieving significant enantioselectivity in excited-state asymmetric photochemistry. Recent research demonstrated that the supramolecular strategy is promising to control the stereochemical outcome of asymmetric photoreaction through relatively strong and long-lasting noncovalent interaction at both ground and excited states. In this methodology, chiral hosts/assemblies provide the chiral environment for photochemically transferring chirality to the complexed photosubstrate in both the ground and the excited states by virtue of relatively strong supramolecular interactions, such as hydrogen bonding, van der Waals, π−π, electrostatic, and hydrophobic interactions. The orientation and conformation of the photosubstrate can be critically manipulated by the supramolecular complexation to ensure the subsequent effective stereoselective photochemical conversion. This Account describes our recent advance in asymmetric photoreactions in supramolecular assemblies. Several chiral photoreactions, including photoisomerization of cycloolefins and photocyclodimerization of anthracene and naphthalene derivatives, have been mediated by various supramolecular hosts, such as cyclodextrin (CD), cucurbituril, pillararene, and chiral polymer. The following advantages of supramolecular asymmetric photochemistry were evidenced: (1) The improvement of stereoselectivity can be enabled by the careful design and fabrication of chiral host molecules. (2) Supramolecular complexation could effectively regulate the orientation and conformation of photosubstrates, thus resulting in novel reaction pathways which create unusual photoproducts that are not achievable through traditional reaction conditions. (3) Asymmetric photoreactions in supramolecular systems showed strong correlations with the external environmental variants, such as temperature, solvent, irradiation wavelength, and pressure, which therefore provide a powerful tool for the regulation of stereoselectivities of excited-state photoreactions. (4) Utilizing supramolecular complexation can dramatically speed up photoreactions, a combination of appropriate photosensitizers/ photocatalysts being able to drive catalyzed chiral photoreactions effectively. (5) Photoisomerization in chiral supramolecular systems has been applied to chiroptical molecular devices, which exhibited multiple stimulus-response functions and advanced switching performances. We believe that these concepts, methods, and principles derived therefrom are instructive in designing chiral supramolecular hosts, elucidating the stereodifferentiation mechanisms in the ground and excited states, and analyzing and improving the stereochemical outcomes of a diverse range of supramolecu...

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Section: Introductionmentioning

confidence: 99%

Asymmetric Photoreactions in Supramolecular Assemblies

Wei

et al. 2023

Acc. Chem. Res.

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“…The importance and versatility of upconversion nanoparticles (UCNPs) have been proven in various applications ranging from displays, 1 bioimaging, 2 sensing, 3 optoelectronics, 4,5 photovoltaics, 6 photocatalysis, 7,8 therapeutics, 9,10 and diagnostics. 11 UCNPs can exhibit antistokes emissions under nearinfrared (NIR) excitation.…”

Section: ■ Introductionmentioning

confidence: 99%

“…The importance and versatility of upconversion nanoparticles (UCNPs) have been proven in various applications ranging from displays, bioimaging, sensing, optoelectronics, , photovoltaics, photocatalysis, , therapeutics, , and diagnostics . UCNPs can exhibit antistokes emissions under near-infrared (NIR) excitation. − They are capable of emitting ultraviolet and visible photons by absorbing multiple NIR photons due to their multiple energy levels or ladder-like energy level systems. , However, the quantum yield of the upconversion emission is generally low due to the multiphoton processes and low absorption cross-section, which hinders the applications of UCNPs.…”

Section: Introductionmentioning

confidence: 99%

Multifunctional Laser-Induced Bubble Microresonator for Upconversion Emission Enhancement

et al. 2023

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Lanthanide-doped upconversion nanoparticles (UCNPs) are attractive luminescent materials for nanophotonic applications under near-infrared excitation, but their full potential is still limited by the low quantum yield of upconversion emission. Herein, we have designed and demonstrated a strategy to enhance the emission of a UCNPs film by a laser-induced microbubble. The microbubble plays multifunctional roles, including collecting plasmonic Ag NPs from the solution by the Marangoni convention, printing them on the UCNPs film to enhance the emission by localized surface plasmon resonances, and serving as a bubble microresonator to enable optical whispering gallery modes (WGMs). Together, the bubble microresonator along with plasmonic Ag NPs can enhance the upconversion emissions by over 200 times. This integrated approach opens new pathways for simultaneous enhancement of emissions from luminescent materials and assembly of NPs over desirable surfaces for optomechanical, biochemical, and sensing applications.

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“…3 Therefore, TTA-UC is highly promising for reducing the energy loss arising from the mismatch between the solar spectrum and solar cell materials and the low applicable efficiency of low-energy solar light. Together with the readily adjustable excitation and emission wavelength, TTA-UC displayed good application potentials in photovoltaics, 4,5 photocatalysis, [6][7][8] bioimaging, 9 and organic light-emitting diodes (OLEDs). 10,11 Nevertheless, TTA-UC technology is still facing great challenges for practical applications.…”

Section: Introductionmentioning

confidence: 99%