CIS ⇌ trans photoisomerization of thioindigoid dyes studied by picosecond flash photolysis

Krysanov, S.A.; Алфимов, М. В.

doi:10.1016/0009-2614(81)85104-4

Cited by 9 publications

(8 citation statements)

References 9 publications

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“…Little information is available in the literature regarding synthesis of the perinaphthothioindigos: typically reference is made to a paper by Harley-Mason and Mann [Harley-Mason, 1942], which does not provide specific details on this synthesis. The form studied here, (1,2-naphtho)(1,8-naphtho)thioindigo, has an absorption spectrum which is in agreement with a compound called PNT by several groups [Krysanov, 1981;Mostoslavskii, 1981;Veniaminov, 1986;]. Veniamanov and Lukov report that the trans form of PNT ( Figure 1A) has a peak at 592 nm and the cis form ( Figure 1B) has a peak at 480 nm, while the bis(perinaphtho)thioindigo isomer shown in Figure 1C has 637 nm (trans) and 513 (cis) peaks.…”

Section: Introductionsupporting

confidence: 83%

“…Thus, even with monochromatic light incident on the sample at the maximum absorption of either form, only photostationary states containing a mixture of the two isomers could be prepared. Perinaphthothioindigo dyes have been reported by several groups [Krysanov, 1981;Mostoslavskii, 1981;Klages, 1982a;Klages, 1982b;Veniaminov, 1986;Takahashi, 1985;Fukunishi, 1989;Irie, 1999]; the absorption spectra and properties differ among the dyes. Little information is available in the literature regarding synthesis of the perinaphthothioindigos: typically reference is made to a paper by Harley-Mason and Mann [Harley-Mason, 1942], which does not provide specific details on this synthesis.…”

Section: Introductionmentioning

confidence: 98%

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Synthesis and Optical Properties of Photochromic Perinaphthothioindigo

Cherepy

Sanner

2005

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(1,2-naphtho)(1,8-naphtho)thioindigo (PNT) has been synthesized following a simple Friedel-Crafts route and its photochemical properties in toluene and PMMA characterized. PNT is a photochromic molecule capable of reversible photoisomerization between a yellow form (cis-PNT, λ max = 484 nm) and a purple form (trans-PNT, λ max = 595 nm). The stable purple form converts to the yellow form with a trans-PNT to cis-PNT conversion quantum yield of 0.027 in toluene and 0.062 in PMMA. The unstable yellow form exhibits a cis-PNT to trans-PNT quantum efficiency of conversion of 0.27-0.85 in toluene and 0.17-0.68 PMMA, with highest conversion efficiency occurring in the vicinity of its λ max of 484 nm. Trans-PNT has a strong fluorescence quantum yield, 0.14 (toluene) and 0.16 (PMMA). For samples prepared photochemically in the cis-PNT form, slow thermal relaxation to the trans form occurs in the dark, with a half life of about 17 hours in toluene (25 °C) and even slower, 168 hours, in PMMA. The property of photoswitching between fluorescent and non-fluorescent forms makes this material a candidate for many applications in imaging and data storage. An anomalous excitation profile for the fluorescence from trans-PNT, showing a dip at ~600 nm, is an agreement with the wavelength-dependent quantum yield of conversion from trans-PNT to cis-PNT, which is highest at the absorbance peak.

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Section: Introductionsupporting

confidence: 83%

Section: Introductionmentioning

confidence: 98%

Synthesis and Optical Properties of Photochromic Perinaphthothioindigo

Cherepy

Sanner

2005

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“…Little information is available in the literature regarding synthesis of the perinaphthothioindigos: typically reference is made to a paper by HarleyMason and Mann [11], which does not provide specific details on this synthesis. The form studied here, (1,2-naphtho)(1,8-naphtho)thioindigo, has an absorption spectrum which is in agreement with a compound called PNT by several groups [5,6,9]. Veniaminov and Lashkov [9] report that the trans form of PNT (Fig.…”

Section: Introductionsupporting

confidence: 66%

“…Photophysical measurements on perinaphthothioindigos have been reported in organic solvent solutions by Krysanov and Alfimov [5] and by Klages et al [7,8]. These studies describe the excited state dynamics as follows.…”

Section: Introductionmentioning

confidence: 95%

“…Thus, even with monochromatic light incident on the sample at the maximum absorption of either form, only photostationary states containing a mixture of the two isomers could be prepared. Perinaphthothioindigo dyes have been reported by several groups [3][4][5][6][7][8][9][10]; the absorption spectra and properties differ among the dyes. Little information is available in the literature regarding synthesis of the perinaphthothioindigos: typically reference is made to a paper by HarleyMason and Mann [11], which does not provide specific details on this synthesis.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis and optical properties of photochromic perinaphthothioindigo

Cherepy¹,

Sanner²

2006

Optical Materials

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1,2-naphtho)(1,8-naphtho)thioindigo (PNT) has been synthesized following a simple Friedel-Crafts route and its photochemical properties in toluene and polymethylmethacrylate (PMMA) have been characterized. PNT is a photochromic molecule capable of reversible photoisomerization between a yellow form (cis-PNT, k max = 484 nm) and a purple form (trans-PNT, k max = 595 nm). The stable purple form converts to the yellow form with a trans-PNT to cis-PNT conversion quantum yield of 0.027 in toluene and 0.062 in PMMA. The unstable yellow form exhibits a cis-PNT to trans-PNT quantum efficiency of conversion of 0.27-0.85 in toluene and 0.17-0.68 PMMA, with highest conversion efficiency occurring in the vicinity of its k max of 484 nm. trans-PNT has a strong fluorescence quantum yield, 0.14 (toluene) and 0.16 (PMMA). For samples prepared photochemically in the cis-PNT form, slow thermal relaxation to the trans form occurs in the dark, with a half life of about 17 h in toluene (25°C) and even slower, 168 h, in PMMA. The property of photoswitching between fluorescent and non-fluorescent forms makes this material a candidate for many applications in imaging and data storage.

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Photocatalytic cis→trans‐Isomerization of Thioindigoid Dyes

Klages

Kobs

Memming

1982

Ber Bunsenges Phys Chem

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The trans‐isomers of certain thioindigoid dyes in dilute solutions can be completely converted to the cis‐isomer by selective excitation of the trans‐isomer. At higher dye concentrations the conversion is limited. The corresponding photostationary state is determined by two processes in opposite directions: (i) by the usual trans→cis photoisomerization and (ii) by an inverse cis→trans isomerization initiated by excitation of the trans‐isomer. An analysis of this peculiar effect has shown that the trans‐triplet catalyses the cis→trans‐isomerization.

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CIS ⇌ trans photoisomerization of thioindigoid dyes studied by picosecond flash photolysis

Cited by 9 publications

References 9 publications

Synthesis and Optical Properties of Photochromic Perinaphthothioindigo

Synthesis and Optical Properties of Photochromic Perinaphthothioindigo

Synthesis and optical properties of photochromic perinaphthothioindigo

Photocatalytic cis→trans‐Isomerization of Thioindigoid Dyes

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