Polymorphism and resulting luminescence properties of 1-acetylpyrene

Tchoń, Daniel; Trzybiński, Damian; Wrona-Piotrowicz, Anna; Makal, Anna

doi:10.1039/c9ce01203f

Cited by 11 publications

(13 citation statements)

References 27 publications

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“…MFC of AP is then based on discrete structural deformation of each polymorph and mechanically‐induced phase transitions between dark and green forms would not occur in this case (Figure 2c). The previous study also supports the comparable thermodynamic stability of AP (dark) and AP (green) and the lack of phase transitions between them [19] . Thus, the small difference in molecular packing motifs induces a large difference in the solid‐state fluorescence and their mechanical response.…”

Section: Resultssupporting

confidence: 77%

“…Acetylpyrenes and pyrenyl ynones with and without tert ‐butyl groups (Figure 1: AP , [19] PY‐Me , [17] PY‐TMS , [17] tAP , [22] tPY‐Me and tPY‐TMS ) were prepared to investigate the MFC properties with different bulkiness and positions (1‐substituted or 2,7‐di‐ tert ‐butyl+4‐substituted pyrenes) based on the reported procedures. We first focused on the simplest compound AP .…”

Section: Resultsmentioning

confidence: 99%

“…The non‐emissive thin plate and green fluorescent block crystals were obtained from ethanol and dichloromethane solutions, respectively. According to the simulated powder X‐ray diffraction (PXRD) patterns using the crystal information files (CIF), [19] the obtained PXRD patterns were assigned to be α type (space group Cc: AP (dark)) and γ type (space group P 2 1 : AP (green)), while β type (space group P 2 1 / c : AP (weak‐green)) was not isolated in this study (see Supporting Information Figure S1a). The characteristic peaks of AP (dark) at 2 θ =6.1, 12.2, 18.2 and 30.6° correspond to the Miller indices (h k l)=(2 0 0), (4 0 0), (6 0 0) and (10 0 0), and those of AP (green) at 2 θ =11.8, 15.2, 29.4 and ∼40° are assigned to be (0 0 3), (0 1 3), (3 1 3) and (3 3 3) planes, respectively.…”

Section: Resultsmentioning

confidence: 99%

“… a) Crystal packing structures of AP (dark), AP (weak‐green) and AP (green) [19] . b) Solid‐state emission spectra of AP (dark) and AP (green) (black: pristine, blue: ground, red: 30 min after grinding at RT, green: another 30 min at 50 °C, λ ex =360 nm) and pictures of pristine/ground forms under UV irradiation λ ex =365 nm (white dotted circle shows non‐emissive plate crystals of AP (dark), arrows show the chromic directions of MFC).…”

Section: Resultsmentioning

confidence: 99%

“…1‐Acetylpyrene ( AP ) is a common simple molecule but has been reported as either emissive or non‐emissive, which recently turned out to be caused by polymorphism [17–19] . Three crystal structures, so‐called α‐type, β‐type and γ‐type, were successfully determined with slight difference in lattice energy, resulting in distinct fluorescence properties depending on the molecular arrangements.…”

Section: Introductionmentioning

confidence: 99%

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Multi‐Directional Mechanofluorochromism of Acetyl Pyrenes and Pyrenyl Ynones

et al. 2021

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A series of acetyl pyrenes and pyrenyl ynones with and without tert‐butyl groups showed distinct mechanofluorochromism (MFC). Four pairs of polymorphic solids were found out of six compounds and interestingly, each of them showed hypsochromic, bathochromic or off‐to‐on MFC. The MFC properties were rationalized by categorizing the packing schemes into herringbone, sandwich, beta and gamma motifs depending on the relative contributions of C⋅⋅⋅C (or π‐π) against C⋅⋅⋅H contacts. The bulky tert‐butyl and trimethylsilyl groups served not only to reduce the number of aggregation patterns but also to prohibit the complete back reactions in solid state. Our results suggest that the simple pyrene derivatives may be promising candidates for a novel group of mechanically‐sensitive materials.

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Section: Resultssupporting

confidence: 77%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Multi‐Directional Mechanofluorochromism of Acetyl Pyrenes and Pyrenyl Ynones

et al. 2021

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Color Polymorphism and Room Temperature Phosphorescence of 4‐Bromo‐2,7‐Di‐Tert‐Butyl‐ 9‐Methoxypyrene

Morawski,

Karpiuk,

Grzybowski

2024

ChemPhysChem

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The title compound has two polymorphic crystal structures having strikingly different absorption and luminescence spectra that result from different packing motifs in the crystal lattice. The polymorph with brick wall‐like packing of molecules is white and shows very weak violet fluorescence whereas the second polymorph, where molecules are arranged in columnar stacks, is bright yellow and displays intense green fluorescence with maximum at 487 nm (20530 cm‐1). In the white polymorph, where the distance between neighboring chromophores is increased, absorption and fluorescence spectra are similar to those of monomer in solution, and intersystem crossing to triplet manifold is the dominant pathway of relaxation. In the yellow polymorph, molecules within the columnar stacks are rotated which mitigates the steric hindrance and leads to closer π‐stacking of the pyrene cores. That increases the ππ overlap and strengthens intermolecular interactions decreasing energy of the excited states. This affects emission spectra and photophysical processes – fluorescence yield grows whereas triplet formation yield decreases when S1 is lowered below higher triplet states and conditions for effective vibronic spin‐orbit coupling are not favorable. The effect is not observed for other similar pyrene derivatives, testifying the uniqueness of the phenomenon.

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Polymorphs with Remarkably Distinct Physical and/or Chemical Properties

Saha

Nath

Thakuria

2022

The Chemical Record

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Polymorphism in crystals is known since 1822 and the credit goes to Mitscherlich who realized the existence of different crystal structures of the same compound while working with some arsenate and phosphate salts. Later on, this phenomenon was observed also in organic crystals. With the advent of different technologies, especially the easy availability of single crystal XRD instruments, polymorphism in crystals has become a common phenomenon. Almost 37 % of compounds (single component) are polymorphic to date. As the energies of the different polymorphic forms are very close to each other, small changes in crystallization conditions might lead to different polymorphic structures. As a result, sometimes it is difficult to control polymorphism. For this reason, it is considered to be a nuisance to crystal engineering. It has been realized that the property of a material depends not only on the molecular structure but also on its crystal structure. Therefore, it is not only of interest to academia but also has widespread applications in the materials science as well as pharmaceutical industries. In this review, we have discussed polymorphism which causes significant changes in materials properties in different fields of solid-state science, such as electrical, magnetic, SHG, thermal expansion, mechanical, luminescence, color, and pharmaceutical. Therefore, this review will interest researchers from supramolecular chemistry, materials science as well as medicinal chemistry.

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Polymorphism and resulting luminescence properties of 1-acetylpyrene

Abstract: Crystal packing, not just the presence of acetyl groups, determines luminescence properties of crystalline 1-acetyl-pyrene.

Cited by 11 publications

References 27 publications

Multi‐Directional Mechanofluorochromism of Acetyl Pyrenes and Pyrenyl Ynones

Multi‐Directional Mechanofluorochromism of Acetyl Pyrenes and Pyrenyl Ynones

Color Polymorphism and Room Temperature Phosphorescence of 4‐Bromo‐2,7‐Di‐Tert‐Butyl‐ 9‐Methoxypyrene

Polymorphs with Remarkably Distinct Physical and/or Chemical Properties

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