Polymorphism and benzene solvent controlled stimuli responsive reversible fluorescence switching in triphenylphosphoniumfluorenylide crystals

Hariharan, P. S.; Mariyatra, Mahimaidoss Baby; Mothi, Ebrahim M.; Neels, Antonia; Rosair, Georgina M.; Anthony, Savarimuthu Philip

doi:10.1039/c7nj01136a

Cited by 12 publications

(7 citation statements)

References 51 publications

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“…50−52 Our system is more suitable to be described as "polymorphism-induced emission enhancement (PIEE)" because BAH-1 appeared to show that a reversible on/ off emission is possible by the crystalline−crystalline transition through water vapor adsorption/desorption. It is noteworthy that reports for polymorphic AIEgen with a reversible on/off emission property 53 are relatively rare compared to those of polymorphic materials with changes in emission wavelength.…”

Section: Resultsmentioning

confidence: 99%

Microcrystal Electron Diffraction Elucidates Water-Specific Polymorphism-Induced Emission Enhancement of Bis-arylacylhydrazone

Cho

Kim

et al. 2021

ACS Appl. Mater. Interfaces

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Aggregation-induced emission (AIE) phenomena have gained intense interest over the last decades because of its importance in solid-state emission. However, the elucidation of a working mechanism is difficult owing to the limited characterization methods on solid-state molecules, further complicated if dynamic structural changes occur. Here, a series of bis-arylacylhydrazones (BAHs) were synthesized, for which their AIE properties are only turned on by the reversible adsorption of water molecules. We used microcrystal electron diffraction (MicroED) to determine the molecular structures of two BAHs directly from bulk powders (without attempting to grow crystals) prepared in the absence or presence of water adsorption. This study reveals the unambiguous characterization of the dependence of crystal packing on the specific cocrystallization with hydrates. The structural analysis demonstrates that water molecules form strong hydrogen bonds with three neighboring BAH-1, resulting in the almost complete planarization and restriction of the intramolecular rotation of the molecule. MicroED plays an important role in providing a decisive clue for the reversible polymorphism changes induced by the adsorption of water molecules, regulating emissive properties.

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Section: Resultsmentioning

confidence: 99%

Microcrystal Electron Diffraction Elucidates Water-Specific Polymorphism-Induced Emission Enhancement of Bis-arylacylhydrazone

Cho

Kim

et al. 2021

ACS Appl. Mater. Interfaces

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“…In the presence of such stimuli, the materials may even undergo changes between different polymorphic modificationsthe existence of at least two different crystal structures of the same material . While the phenomenon of polymorphism is not uncommon in molecular crystals and it is predominantly discovered in pharmaceutical compounds, its existence in organic materials with responsive characteristics is scarce. − Moreover, the ability of the appearance of two polymorphs simultaneously in a given condition, i.e., concomitant polymorphs , and their reversible switching between centrosymmetric and non-centrosymmetric forms in such responsive organic materials are extremely rare. , …”

Section: Introductionmentioning

confidence: 99%

Concomitance, Reversibility, and Switching Ability of Centrosymmetric and Non-Centrosymmetric Crystal Forms: Polymorphism in an Organic Nonlinear Optical Material

Jha

Dutta

Munshi

2017

Crystal Growth & Design

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Reversibility between two concomitant polymorphs and their switching ability is demonstrated for the novel organic nonlinear optical (NLO) material Z-3-(3-methoxyphynyl)-2-(4-nitrophenyl)acrylonitrile. The appearances of their concomitant as well as exclusive polymorphic forms were discovered upon systematic crystallization experiments using various solvents. Determination of X-ray crystal structures confirmed that the polymorphs crystallize in centrosymmetric (P21/n) and non-centrosymmetric (Fdd2) space groups. A search using the Cambridge Structural Database revealed that there exist only 10 such polymorphic pairs. Reversible phase transitions and the switching ability between the polymorphs can be achieved via both heat and solvents as stimuli. Structural analysis confirmed that the polymorphs have two-dimensional similarity. Further, quantitative and qualitative analysis of interaction energies based on the UNI force field and energy frameworks indicate that they possess very similar energies, although the centrosymmetric form is slightly lower in energy. A comparably high value of second harmonic generation activity and the NLO properties as estimated based on gas-phase and in-crystal calculations suggest that the non-centrosymmetric form could be a potential NLO material. To the best of our knowledge, this study is the rarest of its kind to show the reversibility and switching ability between centrosymmetric and non-centrosymmetric polymorphic phases in an organic material, induced via both thermal and solvent stimuli.

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“…Due to differences in packing arrangement, polymorphic materials show variable physicochemical properties which are of significant importance in designing functional materials, pharmaceutical solids, explosives, dyes, and pigments. [25][26][27] Some of the polymorphic organic fluorophores studied in the recent literature include substituted benzothiazole-fluorene based materials, 28 triphenylphosphonium fluorenylide, 29,30 1-acetylpyrene, 31 N,N-dimethylanilino naphthalimide, 17 etc. which show outstanding photo-physical behaviour.…”

Section: Introductionmentioning

confidence: 99%

Solid-state fluorescence of a quasi-isostructural polymorphic biphenyl based Michael addition product

et al. 2022

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Polymorphism and benzene solvent controlled stimuli responsive reversible fluorescence switching in triphenylphosphoniumfluorenylide crystals

Abstract: Triphenylphosphoniumfluorenylide (TPPFY), a fluorescent fluorene attached molecule, showed polymorphism, benzene solvent induced aggregation enhanced emission (AEE) and external stimuli responsive on–off fluorescence switching.

Cited by 12 publications

References 51 publications

Microcrystal Electron Diffraction Elucidates Water-Specific Polymorphism-Induced Emission Enhancement of Bis-arylacylhydrazone

Microcrystal Electron Diffraction Elucidates Water-Specific Polymorphism-Induced Emission Enhancement of Bis-arylacylhydrazone

Concomitance, Reversibility, and Switching Ability of Centrosymmetric and Non-Centrosymmetric Crystal Forms: Polymorphism in an Organic Nonlinear Optical Material

Solid-state fluorescence of a quasi-isostructural polymorphic biphenyl based Michael addition product

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