Unusual piezochromic fluorescence of a distyrylpyrazine derivative crystals: phase transition through [2 + 2] photocycloaddition under UV irradiation

AbstractThe piezochromic fluorescence (FL) of a distyrylpyrazine derivative, 2,3-diisocyano-5,6-distyrylpyrazine (DSP), was investigated in this study. Depending on the recrystallization method, DSP afforded two different crystals with green and orange FL emission. The orange color FL emission crystal (O-form) was easily converted to the green color FL emission one (G-form) by manual grinding. The G-form was also converted to a slightly different orange color FL emission crystal (RO-form) by a weak UV irradiation. When the RO-form was ground again, the G-form was regenerated. The FL colors changed between the G- and RO-forms over several ten times by repeated mechanical grinding and UV irradiation. The FL, UV–visible, 1H-NMR and XRD results showed that the O (or RO)-to-G transformation induced by mechanical stress results from the change of degree of molecular stacking from dense molecular stacking structure to relatively loose molecular stacking structure, whereas the G-to-RO reconversion by UV irradiation results from return to dense molecular stacking structure again due to lattice movement (lattice slipping) allowed by photocycloaddition in solid-state.

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A multinuclear solid-state magnetic resonance study of silver nitrate triphenylphosphine

Canadian Journal of Chemistry ◽

10.1139/v05-174 ◽

2005 ◽

Vol 83 (10) ◽

pp. 1721-1730 ◽

Cited By ~ 4

Author(s):

Se-Woung Oh ◽

Guy M Bernard ◽

Roderick E Wasylishen ◽

Robert McDonald ◽

Michael J Ferguson

Keyword(s):

Phase Transition ◽

Solid State ◽

Single Crystal ◽

Silver Nitrate ◽

Solid Phase ◽

Variable Temperature ◽

Spin Coupling ◽

X Ray Diffraction ◽

X Ray ◽

H Nmr

Variable-temperature solid-state 31P, 15N, and 2H NMR spectroscopy, X-ray diffraction, and differential scanning calorimetry studies of the 1:1 adduct of silver nitrate and triphenylphosphine (AgNO3·PPh3) reveal a solidsolid phase transition at 300 K. The principal components of the phosphorus and nitrogen chemical shift tensors for both phases are determined from NMR spectra of MAS and stationary samples. In addition, the indirect spin-spin coupling between phosphorus and the naturally occurring isotopes of silver (107Ag and 109Ag) are resolved. Experimental 2H NMR line shapes for silver nitrate perdeuterated triphenylphosphine are those characteristic of rigid phenyl groups at temperatures above and below the phase-transition temperature. Powder and single-crystal X-ray diffraction data for AgNO3·PPh3 obtained at 193, 295, and 313 K are reported; data obtained at 193 and 295 K are almost identical, but are significantly different from those obtained at 313 K and from an earlier single-crystal X-ray diffraction investigation performed at 298 K. All X-ray studies found that AgNO3·PPh3 crystallizes in the monoclinic form, space group P21/c.Key words: 1:1 silver nitrate triphenylphosphine adduct, solid-state NMR, X-ray diffraction, phase transition.

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Temperature-Dependent Solid-state Luminescence and Reversible Phase Transition of (n-Bu4N)[Au(SC6H3-3,5-Me2)2]

Chemistry Letters ◽

10.1246/cl.2003.1002 ◽

2003 ◽

Vol 32 (11) ◽

pp. 1002-1003 ◽

Cited By ~ 4

Author(s):

Seiji Watase ◽

Takayuki Kitamura ◽

Nobuko Kanehisa ◽

Masami Nakamoto ◽

Yasushi Kai ◽

...

Keyword(s):

Phase Transition ◽

Solid State ◽

Temperature Dependent ◽

Reversible Phase Transition ◽

Reversible Phase ◽

State Luminescence

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Microstructure, Piezoelectric Properties and Phase Transition of (Pb 0.90 Ba 0.10 )ZrO 3 Ceramics Prepared by Solid State Reaction Method

Ferroelectrics Letters Section ◽

10.1080/07315170216197 ◽

2002 ◽

Vol 29 (5-6) ◽

pp. 105-115 ◽

Cited By ~ 1

Author(s):

T. Bongkarn ◽

G. Rujijanagul ◽

T. Tunkasiri

Keyword(s):

Phase Transition ◽

Solid State ◽

Solid State Reaction ◽

Piezoelectric Properties ◽

Solid State Reaction Method ◽

Reaction Method

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Characterization of some mesogenic alkyl 1-thioglycosides

Canadian Journal of Chemistry ◽

10.1139/v02-157 ◽

2002 ◽

Vol 80 (8) ◽

pp. 1162-1165 ◽

Cited By ~ 2

Author(s):

B Henrissat ◽

G K Hamer ◽

M G Taylor ◽

R H Marchessault

Keyword(s):

Phase Transition ◽

Liquid Crystal ◽

Solid State ◽

Solid State Nmr ◽

Liquid Crystalline ◽

Liquid Crystal Phase ◽

X Ray Diffraction ◽

X Ray ◽

Liquid Crystalline Phases

A series of dodecyl 1-thio-β-D-glycosides has been synthesized and characterized (DSC, NMR, CP MAS, X-ray diffraction) as possible new marking materials with liquid-crystalline properties. These compounds undergo solid to liquid crystal phase transitions at various temperatures, which depend on the nature of the carbohydrate part of the structure. Their liquid-crystalline phases show extreme shear thinning behaviour.Key words: liquid crystal, powder X-ray diffraction, phase transition, thioglycoside, solid-state NMR, marking material

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Water-soluble β-aminobisulfonate building blocks for pH and Cu2+ indicators

RSC Advances ◽

10.1039/c6ra17791c ◽

2016 ◽

Vol 6 (88) ◽

pp. 84712-84721 ◽

Cited By ~ 5

Author(s):

Maria A. Cardona ◽

Marina Kveder ◽

Ulrich Baisch ◽

Michael R. Probert ◽

David C. Magri

Keyword(s):

Nmr Spectroscopy ◽

Building Blocks ◽

Water Soluble ◽

Visible Absorption ◽

H Nmr ◽

Uv Visible

Two phenyl β-aminobisulfonate ligands characterised by UV-visible absorption, EPR and 1H NMR spectroscopy exhibit evidence for binding with Cu2+ in water and methanol.

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Synthesis and properties of a sterically encumbered poly(thienylene vinylene): poly[E-1,2-(4,4prime-dihexyl-2,2prime-dithienyl)ethylene]

Canadian Journal of Chemistry ◽

10.1139/v98-110 ◽

1998 ◽

Vol 76 (11) ◽

pp. 1524-1529

Author(s):

Jimmy Lowe ◽

Carl Bartels ◽

Steven Holdcroft

Keyword(s):

Ftir Spectroscopy ◽

Electrically Conducting ◽

H Nmr ◽

Visible Photoluminescence ◽

Micron Size ◽

Visible Irradiation ◽

Uv Visible ◽

The Stability ◽

Doped Polymer ◽

Polythiophene Derivative

Electrically conducting poly[E-1,2-(4,4prime-dihexyl-2,2prime-dithienyl)ethylene] was synthesized and structurally characterized by UV-visible, 1H NMR, and FTIR spectroscopy. The head-to-head arrangement of the alkylthiophene dyads directly affects the UV-visible, photoluminescence, and electroluminescence maxima of the polymer. The conductivity of the doped polymer was measured to be ~2 S cm-1 and the stability of the oxidized polymer possessing various dopants was compared. UV-visible irradiation of PDHDTE rendered the films insoluble and photolithography was used to produce micron-size images. FTIR was used to monitor the photoproducts during photolysis of PDHDTE. Mechanisms of photooxidation were proposed, based on the photoproducts observed.Key words: polythiophene derivative, head-to-head dyad, photolithography, photooxidation, electroluminescence.

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On light scattering near phase-transition points in the solid state

Physics Letters A ◽

10.1016/0375-9601(74)90196-0 ◽

1974 ◽

Vol 47 (4) ◽

pp. 345-346 ◽

Cited By ~ 17

Author(s):

V.L. Ginzburg ◽

A.P. Levanyuk

Keyword(s):

Phase Transition ◽

Light Scattering ◽

Solid State ◽

Transition Points

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Synthesis, Characterization, and Biological Studies of a Piperidinyl Appended Dipicolylamine Ligand and Its Rhenium Tricarbonyl Complex as Potential Therapeutic Agents for Human Breast Cancer

Bioinorganic Chemistry and Applications ◽

10.1155/2016/2675937 ◽

2016 ◽

Vol 2016 ◽

pp. 1-10 ◽

Cited By ~ 4

Author(s):

Amali Subasinghe ◽

Inoka C. Perera ◽

Svetlana Pakhomova ◽

Theshini Perera

Keyword(s):

Breast Cancer ◽

Anticancer Agents ◽

Human Breast Cancer ◽

Human Breast ◽

Tricarbonyl Complex ◽

Nmr Spectrum ◽

H Nmr ◽

Biological Studies ◽

Visible Spectra ◽

Uv Visible

A novel ligand bearing a central piperidinyl sulfonamide group, N(SO2pip)dpa, and its corresponding Re tricarbonyl complex, [Re(CO)3(N(SO2pip)dpa)]+, have been synthesized in good yield. The methylene CH2signal seen as a singlet (4.54 ppm) in a1H NMR spectrum of the ligand in DMSO-d6appears as two doublets (5.39, 5.01 ppm) in a spectrum of the [Re(CO)3(N(SO2pip)dpa)]+complex and confirms the presence of magnetically nonequivalent protons upon coordination to Re. Structural results revealed that the Re–N bond lengths fall within the normal range establishing coordination of ligand to metal. The presence of intraligandπ→π⁎andn→π⁎transitions is indicated by the absorption peaks around 200–250 nm in UV-visible spectra. Absorption peaks in UV-visible spectra around 300 nm for metal complexes were identified as MLCT transitions. The S–N stretch observed as a strong peak at 923 cm−1for N(SO2pip)dpa appeared at a shorter frequency, at 830 cm−1in an FTIR spectrum of the [Re(CO)3(N(SO2pip)dpa)]+. The intense fluorescence displayed by the N(SO2pip)dpa ligand has quenched upon coordination to Re. Relatively low IC50values given by human breast cancer cells, MCF-7, (N(SO2pip)dpa = 139 μM, [Re(CO)3(N(SO2pip)dpa)]+= 360 μM) indicate that N(SO2pip)dpa and [Re(CO)3(N(SO2pip)dpa)]+are promising novel compounds that can be further investigated on their usage as potential anticancer agents.

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Synthesis of perialkynylated tetrapyrazinoporphyrazines and its Optical Properties

Journal of Chemical Research ◽

10.3184/030823409x449473 ◽

2009 ◽

Vol 2009 (5) ◽

pp. 312-316 ◽

Cited By ~ 3

Author(s):

Chun Keun Jang ◽

Jae Yun Jaung

Keyword(s):

Optical Properties ◽

Nmr Spectroscopy ◽

Laser Desorption ◽

Diels Alder ◽

Visible Spectroscopy ◽

H Nmr ◽

Uv Visible ◽

Tof Ms ◽

Matrix Assisted Laser ◽

Matrix Assisted Laser Desorption

Some phthalocyanines soluble in organic solvents have been developed by peripheral introduction of substituent groups. We report a new method for preparation of the polyphenyl-substituted dicyanopyrazines based on the [2 + 4] Diels-Alder cycloaddition of the tetraphenylcyclopentadienone to an ethynyl compound. The synthesised tetrapyrazinoporphyrazinato metal complexes were characterised by UV-visible spectroscopy, MALDI-TOF-Ms (matrix-assisted laser desorption ionisation time-of-flight mass) spectroscopy, and 1H NMR spectroscopy.

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