Photochromism and fluorescence properties of 1,2-bis(2-alkyl-1-benzothiophene-3-yl)perhydrocyclopentenes

Yamaguchi, Tadatsugu; Hosaka, Manabu; Shinohara, Keigo; Ozeki, Toru; Fukuda, Mitsuhiro; Takami, Shizuka; Ishibashi, Yukihide; Asahi, Tsuyoshi; Morimoto, Masakazu

doi:10.1016/j.jphotochem.2014.04.007

Cited by 7 publications

(10 citation statements)

References 36 publications

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“…In this analysis, the radiative transition rate constant was ignored because of its small contribution in the reaction dynamics. 14 The lifetime of the excited state, τ, corresponds to the reciprocal value of the summation of both rate constants of k CI and k n as expressed by eq 6.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…Here, 1 – χ is the fraction toward the ground state of the open-ring isomer at CI, and k CI and k n are respectively the rate constant directing to the conical intersection and that for the nonradiative decay directly returning to the ground state. In this analysis, the radiative transition rate constant was ignored because of its small contribution in the reaction dynamics . The lifetime of the excited state, τ, corresponds to the reciprocal value of the summation of both rate constants of k CI and k n as expressed by eq . …”

Section: Resultsmentioning

confidence: 99%

“…Diarylethene derivatives , are one of the representative systems whose photochromic properties originate from photoinduced cyclization (ring-closing) and cycloreversion (ring-opening) reactions with high thermal stability and durability to the photodegradation. A number of investigations on the switching of physical and chemical properties through cyclization and cycloreversion reactions have been conducted, − and specific excitation methods have opened new functionality such as multiphoton-gated photochromism, − one-color reversible reactions, and plasmon-coupled photoreactions . Moreover, it was found for several derivatives that the morphology change of the crystals can be induced through the photochromic reaction in the crystalline phase, , and this property is expected to apply into the mesoscopic photodriven actuators. − …”

Section: Introductionmentioning

confidence: 99%

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Solvent Polarity Dependence of Photochromic Reactions of a Diarylethene Derivative As Revealed by Steady-State and Transient Spectroscopies

et al. 2016

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Solvent polarity dependence of photochromic reactions such as cyclization and cycloreversion of a photochromic diarylethene derivative, 1,2-bis(2-methyl-3-benzothienyl)perfluorocyclopentene, was investigated by steady-state spectroscopic and femtosecond laser photolysis methods. For the cyclization reaction, it was revealed that the quantum yield decreased with an increase in solvent polarities, mainly due to the decrease in the fraction of the conformer with C 2 symmetry favorable for the cyclization. This result indicated that the branching ratio for the cyclization and the deactivation to the open-ring isomer at the conical intersection was almost independent of the solvent polarity. On the other hand, it was found for the cycloreversion process that the closed-ring isomer in the S1 state rapidly deactivated into the ground state in competition with the activated process leading to the conical intersection providing a pathway toward both open- and closed-ring minima in the ground state. The cycloreversion reaction quantum yield also decreasing with an increase in the solvent polarity was attributed to larger increase of the direct deactivation into the ground state from the excited state minimum of the closed-ring isomer.

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Section: ■ Results and Discussionmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Solvent Polarity Dependence of Photochromic Reactions of a Diarylethene Derivative As Revealed by Steady-State and Transient Spectroscopies

et al. 2016

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“…2,21-24 Another approach involves the Pd-catalyzed cross-coupling of 1,2dibromocyclopentene (pathway II in Scheme 1). 4, 11,12,25,26 These methods are quite suitable for thiophene and benzothiophene derivatives, including unsymmetric, 23 but they are generally limited to azole compounds (oxazole, imidazole, thiazole) because the starting compounds are difficult to access and the reaction requires harsh conditions. In addition, an alternative synthesis was used for the preparation of diarylcyclopentene derivatives by the reduction of the carbonyl group in diarylcyclopentenones.…”

Section: -4mentioning

confidence: 99%

Facile synthesis of photoactive diaryl(hetaryl)cyclopentenes by ionic hydrogenation

et al. 2016

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“…[1][2][3] Photochromic compounds, such as diarylethenes, spiropyrans, spirooxazines and azobenzenes, have attracted considerable research attention in recent years. [4][5][6][7][8][9] Naphthopyrans also play a significant role in photochromic materials, due to the versatility of the naphthopyran entity. There has been intense research interest in this class of molecules.…”

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confidence: 99%

Synthesis and Photochromic Properties of Conjugated Naphthopyran Derivatives

Zhao

Yang

Shen³

et al. 2018

Journal of Chemical Research

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Three novel types of naphthopyran derivatives containing alkoxyl and phenyl moieties, 13-butyl −6,11-dimethyl-3,3-diphenyl-3,13-dihydrobenzo[h]indeno[2,1-f]chromen-13-ol (NP), 13-butyl-3,3-bis(6-methoxy-[1,1′-biphenyl]-3-yl)-6,6-dimethyl-3,13-dihydrobenzo[h] indeno[2,1-f]chromen-13-ol (NP1) and 13-butyl-3,3-bis(6-methoxy-4′-naphthalenyl-[1,1′-biphenyl]-3-yl)-6,11-dimenthyl-3,13-dihydrobenz[h]indeno[2,1-f]chromen-13-ol (NP2), were synthesised and characterised. Measurements indicated that they possessed an excellent photochromic response, a rapid thermal bleaching rate and good fatigue resistance. Meanwhile, the UV maximum absorption wavelengths of NP1 (562 nm) and NP2 (597 nm) appeared bathochromically shifted compared with NP (536 nm). The bleaching rate of NP1 was found to be approximately twice that of NP. The results indicated that the UV maximum absorption wavelength and bleaching rate increase with increasing length of the phenyl side chain moieties. In PMMA film, the compounds showed almost the same photochromic properties in the solid state as in dichloromethane solution. The UV absorbance with high-contrast switching in solid film could be beneficial for practical applications.

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Photochromism and fluorescence properties of 1,2-bis(2-alkyl-1-benzothiophene-3-yl)perhydrocyclopentenes

Cited by 7 publications

References 36 publications

Solvent Polarity Dependence of Photochromic Reactions of a Diarylethene Derivative As Revealed by Steady-State and Transient Spectroscopies

Solvent Polarity Dependence of Photochromic Reactions of a Diarylethene Derivative As Revealed by Steady-State and Transient Spectroscopies

Facile synthesis of photoactive diaryl(hetaryl)cyclopentenes by ionic hydrogenation

Synthesis and Photochromic Properties of Conjugated Naphthopyran Derivatives

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