Photomodulable Materials. Synthesis and Properties of Photochromic 3H-Naphtho[2,1-b]pyrans Linked to Thiophene Unitsvia an Acetylenic Junction

Frigoli, Michel; Moustrou, C.; Samat, A.; Guglielmetti, R.

doi:10.1002/1522-2675(20001108)83:11<3043::aid-hlca3043>3.0.co;2-z

Cited by 45 publications

(35 citation statements)

References 20 publications

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“…16,17 Mono bromobithiophene and monobromoterthiophene were prepared according to the literature. [18][19][20][21] 2,2-Bithiophene (BT) (Aldrich) was purified through vacuum sublimation. The supporting electrolyte for electrochemical measurements was tetrabutylammonium hexafluorophosphate, Bu 4 NPF 6 (SigmaAldrich, 98 % purity, reagent grade), which was stored in a vacuum dessicator over silica gel.…”

Section: Methodsmentioning

confidence: 99%

Electrochemical and Photovoltaic Properties of Electropolymerized Poly(thienylsilole)s

et al. 2009

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Electrochemical and photoelectrochemical properties were studied of a series of donor-acceptor materials based on polythiophene modified with silole moieties. The materials were prepared by electrochemical anodic polymerization of 2,5-bis([2,2'-bithiophe]-5-yl)-1,1-dimethyl-3,4-diphenylsilole14 and 2,5-bis([2,2'-terthiophene]-5-yl)-1,1-dimethyl-3,4-diphenyl-silole, as well as copolymerization of these monomers with 2,2'-bithiophene. Photocurrent measurements showed that introduction of silole resulted in a considerable enhancement of the photovoltaic properties of silolecontaining materials and especially the fill factor. However, as demonstrated by Mott-Schottky measurements, electropolymerized silole-containing materials showed a substantial degree of disorder and high density of states in the midgap, which negatively affected their photovoltaic properties. Atomic 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60 2 force microscopy (AFM) and phase imaging revealed the presence of phase segregation and heterogeneity of the silole-containing materials. Interestingly, introduction of siloles suppressed the cathodic (n-type) doping typical for polythiophenes. This work demonstrates that siloles show great promise as electron-acceptor groups for all-organic solar cells; however, further work is required to optimize the properties and performance of poly(thienyl-silole) based materials.

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Section: Methodsmentioning

confidence: 99%

Electrochemical and Photovoltaic Properties of Electropolymerized Poly(thienylsilole)s

et al. 2009

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“…Chemicals. The (NPA) 2 T was prepared for previous works (10,11). Its purity was checked by high-performance liquid chromatography (.98%), using a diode array detector.…”

Section: Methodsmentioning

confidence: 99%

“…It has been found that it exhibits a classical photochromic behavior because the starting closed form yields the open (photomerocyanine type) colored form, PM (k max at ;480 nm in toluene) by thermally reversible photocleavage of the C-O bond. A bleaching rate constant of 0.14 s ÿ1 for the thermal back reaction in toluene at 293 K has been reported (10). The compound was also found to exhibit a significant fluorescence emission (11).…”

Section: Introductionmentioning

confidence: 91%

“…The synthesis of this compound was described in previous articles together with preliminary information on its photochromic behavior under continuous irradiation (9)(10)(11). It has been found that it exhibits a classical photochromic behavior because the starting closed form yields the open (photomerocyanine type) colored form, PM (k max at ;480 nm in toluene) by thermally reversible photocleavage of the C-O bond.…”

Section: Introductionmentioning

confidence: 99%

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Comprehensive Photokinetic and NMR Study of a Biphotochromic Supermolecule Involving Two Naphthopyrans Linked to a Central Thiophene Unit Through Acetylenic Bonds¶

Ortica¹,

Moustrou²,

Berthet³

et al. 2003

Photochem Photobiol

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A photophysical and photochemical study of a biphotochromic compound where two naphthopyran units are linked by an acetylene-thiophene-acetylene bridge has been carried out in toluene. Both fluorescence and intersystem crossing to the triplet manifold were found to compete with the photocoloration process. Two photoproducts (transoid-trans and transoid-cis stereoisomers), absorbing at approximately 480 nm and corresponding to the opening of a single photochromic unit, were detected by spectrophotometric analysis after short irradiation time in diluted solution and identified by 1H-nuclear magnetic resonance (NMR) spectroscopy. After prolonged irradiation at 228 K of highly concentrated solutions (up to 3 x 10(-3) mol dm(-3)), two additional isomers, absorbing at approximately 550 nm, were formed. Their NMR spectra indicate the opening of both photochromic units. An interesting effect of selective vibronic excitation was found, showing that the photoreaction is favored at excited vibronic levels to the detriment of the radiative relaxation.

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“…Nowadays, these photochromic compounds are also used in architecture, automotive industry, cosmetics, textiles, decoration, etc [8][9][10][11][12]. Most of the scientific research done on photochromic C. R. Chimie 13 (2010) [212][213][214][215][216][217][218][219][220][221][222][223][224][225][226] NP compounds was devoted to the optimization of its spectral and kinetic properties by substitution of functional groups in the photochromic molecule [13][14][15][16][17][18][19][20][21]. The most remarked properties of these materials, such as the absorption spectra upon irradiation with UV light and the kinetic of the bleaching process (recovery of original whiteness) have been measured in different solvents [4,[22][23][24] or dispersed in organic polymer matrices [7,21,25].…”

Section: Introductionmentioning

confidence: 99%

Thin film photochromic materials: Effect of the sol-gel ormosil matrix on the photochromic properties of naphthopyrans

Pardo

Zayat

Lévy

2009

Comptes Rendus. Chimie

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Photomodulable Materials. Synthesis and Properties of Photochromic 3H-Naphtho[2,1-b]pyrans Linked to Thiophene Unitsvia an Acetylenic Junction

Cited by 45 publications

References 20 publications

Electrochemical and Photovoltaic Properties of Electropolymerized Poly(thienylsilole)s

Electrochemical and Photovoltaic Properties of Electropolymerized Poly(thienylsilole)s

Comprehensive Photokinetic and NMR Study of a Biphotochromic Supermolecule Involving Two Naphthopyrans Linked to a Central Thiophene Unit Through Acetylenic Bonds¶

Thin film photochromic materials: Effect of the sol-gel ormosil matrix on the photochromic properties of naphthopyrans

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