Doping of charge-transfer molecules in cocrystals for the design of materials with novel piezo-activated luminescence

Yin, Xiu; Zhai, Changwei; Hu, Shuhe; Lei, Yue; Xu, Tongge; Yao, Zhen; Li, Quanjun; Liu, Ran; Yao, Mingguang; Sundqvist, Bertil; Liu, Bingbing

doi:10.1039/d2sc06315h

Cited by 11 publications

(6 citation statements)

References 44 publications

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“…The shortened separations hint at improved hydrogen-bond strength when water serves as a hydrogenbond acceptor. These {(CzIp) 3 S3). Each carbazole moiety along the noncovalent ribbon has produced face-to-face π•••π stackings with OFN or TCNQ, and the centroid-to-centroid (Table S4) and interplanar distances are 3.7005(15) and 3.7391(2) Å as well as 3.5270(10) and 3.5270(10) Å.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…Molecular crystals with desirable structures and efficient photoluminescence are highly important for multiscenario field applications in displaying, 1,2 sensing, 3,4 optical waveguide, 5 and optoelectronics devices. 6−10 Lots of organic crystalline materials with tunable emission color, long-lived lifetime, and/or high quantum yield have been designed and manufactured by powerful cocrystal engineering strategy.…”

Section: ■ Introductionmentioning

confidence: 99%

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Solid-State Assembly and Photoluminescent Behavior of 5-(9H-Carbazol-9-yl)isophthalic Acid–Based Molecular Crystals Influenced by Solvents and Organic Counterparts

Tang,

Quan,

Ding

et al. 2024

Crystal Growth & Design

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Molecular crystals with desirable structures and tunable photoluminescence are highly important for multiscenario field applications as lasers, sensors, and light-emitting devices. However, purposeful controls on the photoluminescence are still challenging because of the high sensitivity of molecular stackings to molecular structures and surroundings. Herein, solid-state assembly and photoluminescent behavior of nine 5-(9H-carbazol-9-yl) isophthalic acid (CzIp)based molecular crystals have been crystallographically, spectroscopically, and theoretically investigated by incorporation with electron-deficient acceptors and polar solvent molecules. As compared to the self-aggregation of green-emissive CzIp, methanol-solvated CzIp-CH 3 OH and hydrated CzIp-H 2 O exhibit tailorable structural overlaps for the π-stacked CzIp−CzIp dimers, emitting high-energy cyan and blue fluorescence upon excitation by UV light. These blue-shifted emissions are from different local excited states of the π-stacked dimers. By contrast, six cocrystals with 1:1 and 2:1 stoichiometry and/or cocrystallized solvent are constructed, respectively, from the π−π stacked CzIp-acceptor or CzIp−CzIp pairs, which are assembled into one-dimensional ribbons (

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Section: ■ Results and Discussionmentioning

confidence: 99%

Section: ■ Introductionmentioning

confidence: 99%

Solid-State Assembly and Photoluminescent Behavior of 5-(9H-Carbazol-9-yl)isophthalic Acid–Based Molecular Crystals Influenced by Solvents and Organic Counterparts

Tang,

Quan,

Ding

et al. 2024

Crystal Growth & Design

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“…The authors have further demonstrated that doping small fractions of pyrene into TCNB/naphthalene cocrystals led to a FRET system that yielded white light . These preliminary investigations have been followed by numerous reports of stoichiometric cocrystal development between donors and acceptor molecules to design multicolor emissive solids. – Though charge transfer cocrystals based on donar–acceptor conjugated molecules and halogen bonds are well reported, hydrogen bond-driven cocrystals are rarely reported to tune the optoelectronic properties. – …”

Section: Introductionmentioning

confidence: 99%

Switching the Solid-State Emission of Organic Crystals through Coformer Choice and Vapochromism

Ahmad,

Dar

2023

J. Phys. Chem. C

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Luminescence in aggregated systems is an intriguing phenomenon that can be exploited for the development of smart commercial materials. The establishment of a structure−property relationship is crucial to designing and improvising solid-state emitters. We report an organo-sulfonate hydrate (1) that exists in zwitterionic form and forms an isolated head-to-tail dimer without long-range π-stacking to form a nonemissive solid. Utilizing the understanding of the sulfonatepyridinium supramolecular synthon, the emission of 1 is turned on and off by cocrystallization with 1,10-phenanthroline and 2,2′-bipyridine (2,2′-Bpy) in 2 and 3, respectively. Structural and Hirshfeld studies validate that the packing modulations triggered by the pyridyl precursors are responsible for the emission switching. Charge-transfer dimers formed in 2 stacks through π-interactions to form emissive mixed-stack aggregates (λ max = 610 nm and Φ 1.1%), while the charge−transfer complex formed in 3 exhibits poor π-overlap due to the twisted conformation of 2,2′-Bpy and poor extended π-interactions to form a nonemissive mixed stack 3. The aggregation-induced emission (AIE) is observed in both 1 and 2, which exhibit green emission with maximum intensity at 500 nm (Φ 58.2%) and 465 nm (Φ 77.6%) for a water fraction (f w ) value of 10, i.e., 90:10 (THF/H 2 O v/v). AIE behavior is validated by dynamic light scattering and scanning electron microscopy studies. 1 exhibits vapochromic behavior and undergoes emission turn-on exposure to fumes of organic bases: NH 3 , Et 3 N, and Py. Plausibly due to proton abstraction by the bases, the vapochromic change is reverted by HCl fumes, and the process cycles. The salt forms of 2 and 3 respond to basic fumes only after prior exposure to the fumes of HCl and undergo a red shift (0.98 nm) in 2 and an emission-turn-on (612 nm) in 3. Furthermore, 3 exhibits irreversible thermochromic behavior at 75 °C, which is attributed to the loss of lattice water. The results are supported by the thermal, diffuse reflectance, powder X-ray diffraction, and Hirshfeld studies.

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“…High-pressure can be used to precisely tune intermolecular interactions, altering molecular vibration and rotation modes and electronic excited states, and thus manipulating the emission behaviors. [39][40][41][42][43][44] It is also an efficient technique to tune the delocalization of p electrons and amplify the related effects that are weak at ambient pressure. In this study, we discovered that the "transannular effect", [45][46][47] a type of weak p-p interaction, occurs in phenanthrene molecular crystals because of their unique molecular conguration.…”

Section: Introductionmentioning

confidence: 99%

Realizing long range π-conjugation in phenanthrene and phenanthrene-based molecular crystals for anomalous piezoluminescence

Xu,

Yin,

Zhai

et al. 2023

Chem. Sci.

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Doping of charge-transfer molecules in cocrystals for the design of materials with novel piezo-activated luminescence

Abstract: A novel piezo-activated luminescent material with wide range modulation of the luminescence wavelength and a giant intensity enhancement upon compression was prepared using a strategy of molecular doping. The doping...

Cited by 11 publications

References 44 publications

Solid-State Assembly and Photoluminescent Behavior of 5-(9H-Carbazol-9-yl)isophthalic Acid–Based Molecular Crystals Influenced by Solvents and Organic Counterparts

Solid-State Assembly and Photoluminescent Behavior of 5-(9H-Carbazol-9-yl)isophthalic Acid–Based Molecular Crystals Influenced by Solvents and Organic Counterparts

Switching the Solid-State Emission of Organic Crystals through Coformer Choice and Vapochromism

Realizing long range π-conjugation in phenanthrene and phenanthrene-based molecular crystals for anomalous piezoluminescence

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