Proton triggered circularly polarized luminescence in orthogonal- and co-assemblies of chiral gelators with achiral perylene bisimide

Han, Dongxue; Han, Jianlei; Huo, Shengwei; Qu, Zuoming; Jiao, Tifeng; Liu, Minghua; Duan, Pengfei

doi:10.1039/c8cc02777c

Cited by 56 publications

(47 citation statements)

References 58 publications

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“…However, the CPL properties of obtained chiral materials are some-times unpredictable, and a tedious synthesis process is always inevitable [23,24]. In this context, the combination of chiral host with achiral luminescent guests through chirality transfer to fabricate CPL-active materials recently becomes an arising approach [25][26][27][28][29][30][31].…”

Section: Introductionmentioning

confidence: 99%

“…Considering that the chiral template molecules still require elaborate design and tedious synthesis in the system, developing a simple and versatile chiral host matrix without tedious synthesis should be one of the most important issues in this research field. In addition, most of the reported cases involve a solution phase which definitely limited the practical applications [30,31]. It is emergent to develop solid-state CPL-active materials by a general approach.…”

Section: Introductionmentioning

confidence: 99%

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Dual-Mode Induction of Tunable Circularly Polarized Luminescence from Chiral Metal-Organic Frameworks

et al. 2020

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The general approach for fabricating solid-state materials showing circularly polarized luminescence (CPL) is still in its challenge. In this work, chiral metal-organic frameworks (MOFs) with full-color and white-color circularly polarized light emission are firstly achieved through a host-guest emitter-loading strategy. Chiral zeolitic imidazolate frameworks (ZIFs, a class of MOFs) are fabricated by a facile and simple mixed-ligand coassembly pathway. Meantime, achiral dyes, quantum dots (QDs), and upconversion nanoparticles (UCNPs) are easily loaded into the chiral ZIFs during the synthetic process. Size-matched dyes can be solely encapsulated into the chiral cages of ZIF, resulting in induced CPL and enhanced luminescence efficiency in solid-state ZIF⊃dye composites. Large-sized QDs, after embedding into the gap of the ZIF particles, also exhibited intense CPL activity. Furthermore, through modulating the blending ratio of colored dyes or QDs in chiral ZIFs, white light-emitting ZIFs with circular polarization could be constructed in a solid state. In addition, through loading rare earth element-based upconversion nanoparticles (UCNPs) into chiral ZIFs, upconverted CPL (UC-CPL) could be achieved with a high dissymmetry factor (glum). Thus, various achiral luminophores were endowed with CPL upon coupling with chiral ZIFs, which significantly deepened and enlarged the research scope of the chiroptical materials in a solid state.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Dual-Mode Induction of Tunable Circularly Polarized Luminescence from Chiral Metal-Organic Frameworks

et al. 2020

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“…The tertiary amine group is a strong electron donor and can be easily protonated [33]. In our previous research, it was found that morphologies and properties of aggregates can be significantly influenced by hydrochloric acid and the molecular structure of PBI with tertiary amine groups.…”

Section: Introductionmentioning

confidence: 99%

Organic Acid Regulated Self-Assembly and Photophysical Properties of Perylene Bisimide Derivatives

Wang

Yang

et al. 2020

Materials

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In this work, perylene bisimide derivatives (PBI-1 and PBI-2) with tertiary amine groups were designed and synthesized. To control the final morphologies and properties of their aggregates, seven kinds of organic acids were used to alter the self-assembly environment. The influence of organic acids on the morphology of the aggregates was investigated. Photophysical properties of the aggregates were markedly affected by the kind and concentration of the organic acid. The thermal and gas sensitivities of the PBI-1 aggregates were studied with the use of UV–visible spectroscopy and digital imaging. The shift of the UV–visible spectra varied with time, temperature, acid type and acid concentration. Furthermore, PBI-1 aggregates showed a red-to-blue color change after addition of seven organic acids, whereas the color of the PBI-2 aggregates remained red. These changes of morphologies, photophysical properties and their thermal and gas sensitivities make these aggregates potentially useful in the fields of optoelectronics or sensors.

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“…However,during the formation of higher-order hierarchical assemblies,t heir supramolecular chirality could be either switched or transformed. [4] However,among the reported examples helicity and ground-state chirality switching have been the main focuses, [5,6] and the inversion and switching of the excited-state chirality and circularly polarized luminescence (CPL) has been rarely studied. [2] In another case, although the constituent molecules of luciferin, acting as emitters,h ave the same molecular chirality,t hey emit circularly polarized light of opposite sense when incorporated into macroscopic mirror-image structures.…”

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confidence: 99%

“…[3] Both of these different structural and functional characteristics essentially result from their supramolecular chirality rather than the intrinsic molecular chirality.I nspired by the fascinating natural phenomena, the exploration of supramolecular systems featuring chirality switching,i np articularly inversion, from enantiomeric pure building blocks has attracted great attention recently. [4] However,among the reported examples helicity and ground-state chirality switching have been the main focuses, [5,6] and the inversion and switching of the excited-state chirality and circularly polarized luminescence (CPL) has been rarely studied. [7] Coordination and p-p stacking are widely applied in supramolecular assemblies because of their unique directionality and stacking modes.…”

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confidence: 99%

Self‐Assembly through Coordination and π‐Stacking: Controlled Switching of Circularly Polarized Luminescence

Niu

Jiang

et al. 2019

Angewandte Chemie

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Multiple noncovalent interactions can drive selfassembly through different pathways.H ere,b yc oordinationassisted changes in p-stacking modes between chromophores in pyrene-conjugated histidine (PyHis), aself-assembly system with reversible and inversed switching of supramolecular chirality,a sw ell as circularly polarized luminescence (CPL) is described. It was found that l-PyHis self-assembled into nanofibers showing P-chirality and right-handed CPL. Upon Zn II coordination, the nanofibers changed into nanospheres with M-chirality,a sw ell as left-handed CPL. The process is reversible and the M-chirality can change to P-chirality by removing the Zn II ions.E xperimental and theoretical models unequivocally revealed that the cooperation of metal coordination and p-stacking modes are responsible the reversible switching of supramolecular chirality.T his work not only provides insight into how multiple noncovalent interactions regulate self-assembly pathways.Supportinginformation and the ORCID identification number(s) for the author(s) of this article can be found under: https://doi.Figure 4. Proposed mechanism for supramolecular chirality inversion.a) The dihedral angle between two T-shapedP yHis planes is 838 8,the face-center distance between two parallel pyrene moieties is 5.09 . b) CH-p (T-type) interactions and hydrogen bonding in the crystal of PyHis. c,d) Possible assembly route for nanosphere formation and DFT calculated model for [Zn(PyHis) 5 ] 2+ ,the pyrene rings are replaced by benzene rings for convenientcalculation. Ha toms not involvedi n hydrogen bonding are omitted for clarity.

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Proton triggered circularly polarized luminescence in orthogonal- and co-assemblies of chiral gelators with achiral perylene bisimide

Cited by 56 publications

References 58 publications

Dual-Mode Induction of Tunable Circularly Polarized Luminescence from Chiral Metal-Organic Frameworks

Dual-Mode Induction of Tunable Circularly Polarized Luminescence from Chiral Metal-Organic Frameworks

Organic Acid Regulated Self-Assembly and Photophysical Properties of Perylene Bisimide Derivatives

Self‐Assembly through Coordination and π‐Stacking: Controlled Switching of Circularly Polarized Luminescence

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