AIEgen based polymorphs with solvent regulated crystal-to-crystal switch properties

Lai, Liming; Fang, Bing; Cheng, Wenyu; Li, Pengyu; Zhang, Yantu; Yin, Meizhen

doi:10.1039/d0qm00154f

Cited by 20 publications

(9 citation statements)

References 54 publications

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“…Recently, many co-crystallized materials have been employed for the tuning of solid-state properties recently, such as fluorescence, mechanical chemical behaviors, and electron transfer. − It is a practical method for the modulation of RTP properties through choosing different long-lived phosphors in co-crystallized materials. − Considering the similar structures, good crystallization, and different RTP properties, CzBzCl and CzBzBr are chosen for the construction of co-crystal to modulate RTP properties. A series of CzBzCl / CzBzBr co-crystals with different mass ratios were obtained.…”

Section: Results and Discussionmentioning

confidence: 99%

Modulating Room-Temperature Phosphorescence through the Synergistic Effect of Heavy-Atom Effect and Halogen Bonding

et al. 2021

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Organic room-temperature phosphorescence (RTP) materials have been paid great attention for their promising applications in anticounterfeiting, optical device, and bioimaging. However, owing to inefficient intersystem crossing (ISC), it still remains a challenge to develop organic RTP materials with both high quantum yields (Φ p ) and long lifetime (τ p ). Herein, a reasonable strategy is presented to modulate and balance the Φ p and τ p through the synergy effect of halogen bonding and heavyatom effect (HAE). Modulated RTP properties are successfully achieved by the introduction of halogen atoms into 4-(9-Hcarbazol-9-yl) benzonitrile due to enhanced ISC. Especially, CzBzBr shows the highest Φ p of 23.50% and CzBzCl exhibits the longest τ p of 607.4 ms. The excessive HAE of the bromine atom decreases the τ p of CzBzBr, while moderate HAE of the chlorine atom endows CzBzCl with both high Φ p and long τ p . In addition, the halogen bondings lead to specific halogen-mediated molecular cluster packing, further suppressing nonradiative transition for ultralong RTP emission. Through simple physical co-crystallization with adjusting the mass ratio of CzBzCl/CzBzBr, co-crystals with modulated RTP properties and white-light emission phenomena are obtained. Our study provides a rationale method to develop modulated high-efficiency RTP materials, which will expand their practical applications.

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Section: Results and Discussionmentioning

confidence: 99%

Modulating Room-Temperature Phosphorescence through the Synergistic Effect of Heavy-Atom Effect and Halogen Bonding

et al. 2021

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“…Luminogens with an AIE effect (AIEgens) are opposite to ACQ molecules, which exhibit strong emission in the solid state due to the restriction of intramolecular motion (RIM) . Besides, the inherent twisted structures of AIEgens endow them with a certain degree of mobility in the solid state, making them promising candidates for solid-state study and applications . Meanwhile, according to the RIM mechanism, the emission behavior of AIEgens depends on intramolecular motion.…”

Section: Introductionmentioning

confidence: 99%

“…25 Besides, the inherent twisted structures of AIEgens endow them with a certain degree of mobility in the solid state, making them promising candidates for solid-state study and applications. 26 Meanwhile, according to the RIM mechanism, the emission behavior of AIEgens depends on intramolecular motion. Thus, the molecular motion in the solid state can be in turn reflected by the fluorescence variation.…”

Section: ■ Introductionmentioning

confidence: 99%

Visualization and Manipulation of Solid-State Molecular Motions in Cocrystallization Processes

Wang

Zhang

et al. 2021

J. Am. Chem. Soc.

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Solid-state molecular motions (SSMM) play a critical role in adjusting behaviors and properties of materials. However, research on SSMM, especially for multicomponent systems, suffers from various problems and is rarely explored. Herein, through collaboration with cocrystal engineering, visualization and manipulation of SSMM in two-component systems, namely, FSBO ((E)-2-(4-fluorostyryl)benzo[d]oxazole)/TCB (1,2,4,5-tetracyanobenzene) and PVBO ((E)-2-(2-(pyridin-4-yl)vinyl)benzo[d]oxazole)/ TCB, were realized. The obtained yellow-emissive F/T (FSBO/TCB) cocrystal displayed turn-on fluorescence, and the green-emissive P/T (PVBO/TCB) cocrystal presented redder emission, both of which exhibited an aggregation-induced emission property. At varied pressure and temperature, the grinding mixtures of FSBO/TCB and PVBO/TCB displayed different molecular motions that were readily observed through the fluorescence signal. Notably, even without grinding, FSBO and TCB molecules could move over for 4 mm in a 1D tube. The unique emission changes induced by SSMM were applied in information storage and dynamic anticounterfeiting. This work not only visualized and manipulated SSMM but offered more insights for multicomponent study in aggregate science.

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“…As a more efficient strategy to achieve controllable and inverted handedness, supramolecular co-assembly offers a convenient platform to precisely regulate the arrangement of programmable building blocks via noncovalent interactions (π–π stacking, hydrogen bonds, hydrophobic interactions, van der Waals interactions, and metal coordination). − On account of the dynamic and reversible features of noncovalent interactions, the supramolecular chirality and CPL properties of artificial supramolecular co-assembly systems can be rationally modulated by various stimuli, such as light irradiation, chiral or achiral additives, stoichiometry, assembling rate, and metal ions. − Liu’s group reported that the chirality of cinnamic acid derivatives could be inverted with morphology changed from superhelices to nanokebabs upon ultraviolet light irradiation . Feng’s group fabricated l-phenylalanine hydrogels with controlled supramolecular chirality by cooperating with metal ions .…”

Section: Introductionmentioning

confidence: 99%

Triple-Modulated Chiral Inversion of Co-Assembly System Based on Alanine Amphiphile and Cyanostilbene Derivative

Qin

et al. 2021

ACS Appl. Mater. Interfaces

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The construction of chiroptical materials with controllable chirality is of special importance in biology and chemistry. Although tunable chirality can be realized in various systems, it remains a fundamental challenge to realize multimodulated chiral inversion. Herein, we report that chiral alanine derivative and fluorescent cyanostilbene derivative co-assemble to prepare supramolecular chiral systems, where twist nanofibers with totally inverted supramolecular chirality and circularly polarized luminescence are obtained through stoichiometric modulation. The supramolecular handedness can be inverted by means of altering the cooling rate and incorporating metal ions. The mechanism study reveals that the synergistic effect among hydrogen bonds, coordination interactions, and π–π stacking interactions contributes to the chirality inversion. This work establishes an effective strategy to precisely modulate supramolecular chirality in multiple ways, which shows great potential in developing smart chiroptical materials capable of achieving complex functionalities.

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AIEgen based polymorphs with solvent regulated crystal-to-crystal switch properties

Abstract: An AIEgen with tunable polymorphism-dependent emission and solvent regulated crystal-to-crystal switch properties is reported. Our study has provided insight into the relationship between molecular stacking and emission properties.

Cited by 20 publications

References 54 publications

Modulating Room-Temperature Phosphorescence through the Synergistic Effect of Heavy-Atom Effect and Halogen Bonding

Modulating Room-Temperature Phosphorescence through the Synergistic Effect of Heavy-Atom Effect and Halogen Bonding

Visualization and Manipulation of Solid-State Molecular Motions in Cocrystallization Processes

Triple-Modulated Chiral Inversion of Co-Assembly System Based on Alanine Amphiphile and Cyanostilbene Derivative

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