The Structure and Photochromism of 2,4,4,6-Tetraphenyl-4H-thiopyran

1992 ◽  
Vol 57 (6) ◽  
pp. 1326-1334 ◽  
Author(s):  
Jaroslav Vojtěchovský ◽  
Jindřich Hašek ◽  
Stanislav Nešpůrek ◽  
Mojmír Adamec
Keyword(s):  
Solid State ◽  
Uv Light ◽  
Order Reaction ◽  
Boat Conformation ◽  
X Rays ◽  
Exponential Time ◽  
First Order ◽  
Double Plane ◽  
The Mean ◽  
Independent Molecules

2,4,4,6-Tetraphenyl-4H-thiopyran, C29H22S, orthorhombic, Pna21, a = 17.980(4), b = 6.956(2), c = 34.562(11) Å, V = 4323(2) Å3, Z = 8, Dx = 1.237 g cm-3, F(000) = 1696, λ(CuKα) = 1.54184 A, μ = 1.372 mm-2, T = 294 K. The final R was 0.050 for the unique set of 3103 observed reflections. The central 4H-thiopyran ring forms a boat conformation for both symmetrically independent molecules with average boat angles 4.4(3) and 6.8(3)° at S and C(sp3), respectively. The mean planes of phenyls at the position 2 and 6 are turned from the double plane of 4H-thiopyran by 42.5(5) and 35.8(3)°, respectively. The investigated material undergoes a photochromic change in the solid state after irradiation with UV light or X-rays. The maximum of the new absorption band is situated at 564 nm. The non-exponential time dependence of photochromic bleaching is analysed in terms of a dispersive first-order reaction.

Efficient Synthesis and Photochromic Properties of a New Diarylethene Bearing a Condensed Aromatics Moiety

2012 ◽  
Vol 455-456 ◽  
pp. 33-36
Author(s):  
Ren Jie Wang ◽  
Hong Ying Xia ◽  
Gang Liu ◽  
Shi Qiang Cui
Keyword(s):  
Uv Light ◽  
Optical Storage ◽  
Hybrid Structure ◽  
Order Reaction ◽  
Pmma Film ◽  
Efficient Synthesis ◽  
Photochromic Properties ◽  
First Order ◽  
New Class ◽  
Hexane Solution

A new class of diarylethenes based on a hybrid structure of thiophene and naphthalene has been developed and its properties including photochromism, kinetics and fluorescence were investigated in detail. The results showed that the compound exhibited obvious photochromism, changing from colorless to red after irradiation with 297 nm UV light both in solution and in PMMA film. The kinetic experiments indicated that the cyclization/cycloreversion process of the compound was determined to be the zeroth/first order reaction in hexane solution. At last, the results demonstrated that the diarylethene compound had attractive properties for potential application in optical storage.

Effect of Cyclodextrins on Photodegradation of 4,4-Bis(4-Hydroxyphenyl)Pentanoic Acid under UV Irradiation

2014 ◽  
Vol 665 ◽  
pp. 455-458
Author(s):  
Li Guo ◽  
Jin Huang ◽  
Jun Wu ◽  
Lei Lei Luo
Keyword(s):  
Aqueous Solutions ◽  
Fluorescence Spectra ◽  
High Efficiency ◽  
Uv Light ◽  
Order Reaction ◽  
Pentanoic Acid ◽  
Pseudo First Order Reaction ◽  
First Order ◽  
Inclusion Interaction ◽  
Pseudo First Order

The photodegradation of 4,4-bis (4-hydroxyphenyl) pentanoic acid (DPA) with two cyclodextrins (α-CD and β-CD ) in aqueous solutions induced by UV-light was studied in this paper by means of fluorescence spectra and high efficiency liquid chromatography. The result suggested that DPA with α-CD or β-CD formed inclusion compound in aqueous solutions. The photodegradation of DPA with two cyclodextrins or without cyclodextrin was pseudo-first order reaction. The photodegradation of DPA was accelerated by the addition of β-CD in aqueous solutions, but the that of DPA was inhibited in case of adding α-CD. These differences were due to the differences in inclusion interaction of DPA with α-CD or β-CD.

Synthesis, Properties and Application in Optical Memory of a Photochromic Diarylethene Bearing Pyrimidine and Pyridine Ring

2012 ◽  
Vol 490-495 ◽  
pp. 3733-3737
Author(s):  
Shu Hong Jing ◽  
Shou Zhi Pu ◽  
Shi Qiang Cui
Keyword(s):  
Uv Light ◽  
Optical Memory ◽  
Order Reaction ◽  
Pmma Film ◽  
Zeroth Order ◽  
First Order ◽  
Synthesis Properties ◽  
Fluorescence Switching ◽  
Photochromic Reaction ◽  
Hexane Solution

A new photochromic diarylethene compound, 1-(2,4-dimethoxy-5-pyrimidine)-2-[2-methyl-5-(3-pyridine)-3-thienyl]perfluorocyclopentene(1a), was synthesized, and its photochromic reactivity, fluorescent and electrochemical property were also investigated. Diarylethene 1a changed the color from colorless to pink upon irradiation with UV light, in which absorption maxima were observed at 520 and 519 nm in hexane and PMMA film, respectively. The the photochromic reaction kinetics indicated that the cyclization processes of 1 belong to the zeroth order reaction and the cycloreversion process belong to the first order reaction. This new photochromic system also exhibited remarkable fluorescence switching in hexane solution and this new photochromic system also exhibited remarkable optical storage character.

Synthesis and Properties of 1-(2-Methyl-3-benzothiophene)-2-[2-methyl-5-(3-fluoro-4-chloro)phenyl-3-thienyl]perfluorocyclopentene

2014 ◽  
Vol 1078 ◽  
pp. 98-101
Author(s):  
Guan Ming Liao ◽  
Chun Hong Zheng ◽  
Shou Zhi Pu
Keyword(s):  
Absorption Band ◽  
Emission Intensity ◽  
Uv Light ◽  
Order Reaction ◽  
First Order Reaction ◽  
Fluorescent Properties ◽  
Visible Absorption ◽  
First Order ◽  
Photostationary State ◽  
Closed Ring

An asymmetrical photochromic diarylethene1-(2-Methyl-3-benzothiophene)-2-[2-methyl-5-(3-fluoro-4-chloro) phenyl-3-thienyl] perfluorocyclopentene (1o) was synthesized and its phtochromic, fluorescent properties were investigated in detail. This compound exhibited remarkable photochromism, upon irradiation with 297 nm UV light, the colorless solution of 1o turned to violetred with a new visible absorption band centered at 538 nm (ε = 1.17 × 104 L mol-1 cm-1) attributable to the closed-ring isomer 1c. The kinetic experiments showed that the cyclization and cycloreversion processes were zeroth and first order reaction, respectively. Moreover, diarylethene 1o also exhibited obviously fluorescence switches along with the photochromism.The emission intensity of diarylethene 1o in a photostationary state was quenched to ca. 27% in hexane.

Synthesis and Photochromism Studies of 1-(2-methyl-3-benzofuran)-2-[2-methyl-5-naphthyl-3-thienyl]perfluorocyclopentene

2014 ◽  
Vol 1078 ◽  
pp. 86-89
Author(s):  
Xiao Rong Dong ◽  
Hong Yan Xu ◽  
Shou Zhi Pu
Keyword(s):  
Absorption Band ◽  
Uv Light ◽  
Amorphous Film ◽  
Order Reaction ◽  
Pmma Film ◽  
Zeroth Order ◽  
Fluorescent Properties ◽  
Visible Absorption ◽  
First Order ◽  
Photochromic Reaction

A novel photochromic diarylethene was synthesized and its photochromic and fluorescent properties were investigated. The results showed that this compound exhibited reversible photochromism, changing from colorless to amaranth after irradiation with UV light both in solution and PMMA amorphous film. In hexane, compound 1a exhibited an absorption peak at 266 nm, upon irradiation with 297 nm light, a new visible absorption band centered at 530 nm emerged while the original peak at 266 nm decreased. In PMMA amorphous film, diarylethene 1a also showed good photochromism as similar to that in solution. The photochromic reaction kinetics indicated that the cyclization processes of 1a belong to the zeroth order reaction and the cycloreversion process belong to the first order reaction. Diarylethene 1a also exhibited good fluorescent switching both in solution and in PMMA film upon alternating irradiation with UV and visible light.

Synthesizes and Properties Research of a Photochromic Diarylethene Bearing a Hexatomic Ring

2013 ◽  
Vol 830 ◽  
pp. 278-281
Author(s):  
Zhi Yuan Sun ◽  
Wei Wei Geng ◽  
Shou Zhi Pu
Keyword(s):  
Reaction Kinetics ◽  
Fluorescence Intensity ◽  
Uv Light ◽  
Order Reaction ◽  
First Order Reaction ◽  
First Order ◽  
Solid Films ◽  
Kinetics Of

A new photochromic diarylethene compound 1-(2-cyan-3-phenyl)-2-[5-(4-cyanobenzene) -2-methyl-3-thienyl] perfluorocyclopentene was synthesized. And their properties inculding photochromis, fluorescence in both hexane and solid films, reaction kinetics of cyclization and cycloreversion were studied. And its absorption maxima were observed at 539 nm in hexane and at 552 nm in PMMA films, respectively, upon irradiation with 313 nm UV light. The fluorescence intensity of diarylethene decreased upon irradiation with 313 nm UV light. Besides, the cyclization and cycloreversion processes of the compound were determined to be the zeroth and first order reaction by UV-Vis spectra, respectively.

Study on Photochromic Materials with Synthesizes and Properties of a Novel Unsymmetrical Photochromic Diarylethene

2013 ◽  
Vol 327 ◽  
pp. 78-82
Author(s):  
Zhi Yuan Sun ◽  
Xiao Dan Zhang ◽  
Shi Qiang Cui ◽  
Shou Zhi Pu
Keyword(s):  
Methyl Methacrylate ◽  
Absorption Maximum ◽  
Uv Light ◽  
Order Reaction ◽  
First Order Reaction ◽  
Pmma Film ◽  
First Order ◽  
Open Ring ◽  
Photochromic Materials ◽  
Hexane Solution

A novel unsymmetrical photochromic diarylethene 1-(2-methyl-3-benzofuran)-2-[5-(2-methylbenzene)-2-methyl-3-thieny perfluorocyclopentene1owas synthesized, then its photochromic, Kinetics and fluorescence properties were investigated. The results showed that the diarylethene compound had good photochromism upon irradiation with 297 nm UV light, in which the absorption maximum were observed at 510 nm in hexane solution and 524 nm in poly methyl methacrylate (PMMA) film. Besides, the cyclization and cycloreversion process of the compound were determined to be the zeroth and first order reaction by UV-Vis spectra, respectively. And, the open-ring isomer of the diarylethene exhibited relatively stronger fluorescence at 427 nm when excited at 273 nm in hexane solution.

scholarly journals N 1,N 4,3,6-Tetramethyl-1,2,4,5-tetrazine-1,4-dicarboxamide

2012 ◽  
Vol 68 (6) ◽  
pp. o1841-o1842
Author(s):  
Na-Bo Sun ◽  
Guo-Wu Rao ◽  
Qun Shen
Keyword(s):  
Hydrogen Bonds ◽  
Dihedral Angles ◽  
Maximum Deviation ◽  
Boat Conformation ◽  
Two Dimensional ◽  
Asymmetric Unit ◽  
Compound C ◽  
Dimensional Network ◽  
The Mean ◽  
Independent Molecules

The asymmetric unit of the title compound, C8H14N6O2, contains two independent molecules. In one molecule, the amide-substituted N atoms of the tetrazine ring deviate from the plane [maximum deviation = 0.028 (1) Å] through the four other atoms in the ring by 0.350 (2) and 0.344 (2) Å, forming a boat conformation, and the mean planes of the two carboxamide groups form dihedral angles of 10.46 (13) and 20.41 (12)° with the four approximtely planar atoms in the tetrazine ring. In the other molecule, the amide-substituted N atoms of the tetrazine ring deviate from the plane [maximum deviation = 0.033 (1) Å] through the four other atoms in the ring by 0.324 (2) and 0.307 (2) Å, forming a boat conformation, and the mean planes of the two carboxamide groups form dihedral angles of 14.66 (11) and 17.08 (10)° with the four approximately planar atoms of the tetrazine ring. In the crystal, N—H...O hydrogen bonds connect molecules to form a two-dimensional network parallel to (1-1-1). Intramolecular N—H...N hydrogen bonds are observed.

Synethesis and Properties of 1-(2-trifluoromethylphenyl)-2-[2-methyl-5-(3-N,N-dimethylphenyl)-3-thienyperfluorocyclopentene

2013 ◽  
Vol 473 ◽  
pp. 77-80
Author(s):  
Zhi Yuan Sun ◽  
Dan Dan Xue ◽  
Shou Zhi Pu
Keyword(s):  
Reaction Kinetics ◽  
Fluorescence Intensity ◽  
Uv Light ◽  
Order Reaction ◽  
First Order Reaction ◽  
Fluorescent Properties ◽  
First Order ◽  
Kinetics Of

An unsymmetrical photochromic diarylethene 1-(2-trifluoromethylphenyl)-2-[2-methyl-5-(3-N,N-dimethylphenyl)-3-thienyperfluorocyclopentene (1a) was synthesized and its photochromism, fluorescent properties and reaction kinetics of cyclization and cycloreversion were studied in detail. The compound exhibited remarkable photochromism and its absorption maxima were observed at 552 nm in hexane and at 569 nm in PMMA films upon irradiation with 297 nm UV light. The fluorescence intensity of diarylethene decreased upon irradiation with 297 nm UV light. In addiation, reaction kinetics of the cyclization and cycloreversion processes of the compound were determined to be the zeroth and first order reaction by UV-Vis spectra, respectively.

Sign in / Sign up

Export Citation Format

Share Document