Spectroscopic Studies on Dyes. IV. The Fluorescence Spectra of Thioindigo Dyes<sup>1</sup>

Rogers, Delbert A.; Margerum, J. D.; Wyman, George M.

doi:10.1021/ja01567a031

Cited by 48 publications

(38 citation statements)

References 2 publications

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“…Although vast numbers of photochromic molecules are reported to change colors, molecules which change fluorescence spectra are limited. [4][5][6][7][8][9][10] Recently photochromic or photoswitchable fluorescent molecules have attracted much attention because of their potential use for single-molecule optical memory media as well as super-resolution fluorescence imaging.…”

Section: Introductionmentioning

confidence: 99%

Photoswitchable fluorescent diarylethene derivatives with short alkyl chain substituents

Takagi

Kunishi

Katayama

et al. 2012

Photochem Photobiol Sci

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The sulfone derivatives of 1,2-bis(2-alkyl-6-phenyl-1-benzothiophen-3-yl)perfluorocyclopentene having various short alkyl chain substituents at reactive carbons were prepared and the effect of alkyl substitution on the fluorescence property of the closed-ring isomers was studied. Upon irradiation with ultraviolet (UV) light the derivatives exhibit a brilliant green fluorescence under irradiation with visible (> 400 nm) light, while the fluorescence disappears upon irradiation with visible (> 400 nm) light alone. The fluorescence quantum yield of the methyl substituted derivative (1b) dramatically decreases from 0.84 to 0.15 when the solvent is changed from hexane to acetonitrile, while the changes of ethyl, n-propyl and n-butyl substituted derivatives (2b)–(4b) are moderate. The quantum yields of (2b)–(4b) are kept to values close to 0.7 even in polar acetonitrile. The fluorescence lifetime measurement revealed that efficient non-radiative decay processes took place in (1b) in polar solvent, while their contribution to the deactivation was not so large in (2b)–(4b). The neighboring short alkyl chains at the connecting carbons are considered to defend the sulfone units against the attack of polar solvent molecules and weaken the solvent polarity effect.

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Section: Introductionmentioning

confidence: 99%

Photoswitchable fluorescent diarylethene derivatives with short alkyl chain substituents

Takagi

Kunishi

Katayama

et al. 2012

Photochem Photobiol Sci

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“…NTI was synthesized according to the method described in ref. 23 and purified by high-performance liquid chromatography (HPLC) (solvent, ethylacetate/toluene = 98/2). A toluene solution containing NTI (5×10 −5 mol/l) and 10 wt% polystyrene was spin-coated onto a glass substrate.…”

Section: Recording Mediamentioning

confidence: 99%

“…These spots could be erased. In the present study we chose photochromic perinaphthothioindigo (NTI) [19][20][21][22][23] as the recording medium and tried to detect recorded spots by…”

Section: Introductionmentioning

confidence: 99%

Rewritable Near-Field Optical Recording on Photochromic Perinaphthothioindigo Thin Films: Readout by Fluorescence

Irie¹,

Ishida²,

Tsujioka

1999

Jpn. J. Appl. Phys.

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Near-field optical recording on polystyrene thin films containing photochromic perinaphthothioindigo (NTI) was carried out. NTI underwent a reversible trans/cis photoisomerization in the polystyrene film, and only the trans-form emitted fluorescence. First, polystyrene film containing trans-form NTI molecules was used as the recording medium. Upon irradiation with 633 nm light from a fiber probe tip (aperture diameter ∼100 nm), the fluorescent trans-forms in a small region were converted into nonfluorescent cis-forms. The recorded small regions were detected as dark spots as small as 110 nm by scanning across the written area. Second, polystyrene film containing cis-form NTI molecules was used as the recording medium. Upon irradiation with ultrasmall 488 nm light (aperture diameter ∼80 nm), bright spots as small as 50 nm were recorded and read out with scanning 633 nm light. The bright spots were due to the fluorescence of the photogenerated trans-form NTI molecules. Both the dark and bright spots were erased by irradiation with 488 nm and 633 nm light, respectively. The bright spot could also be recorded using a pulse Nd 3+ : YAG laser (532 nm, pulse width 20 ns).

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“…The great photochemical stability of indigotin can be explained by formula 30 illustrating the fixation of the trans form by hydrogen bonds (for a recent discussion see LUTTKE and KLESSINGER [32]). A non-planar configuration was proposed [35] for the cis-isomer 32. The relative concentrations of these isomers were found to depend on the temperature and on the wave length of the light used for irradiation.…”

Section: C) Indigoid Systemsmentioning

confidence: 99%

“…He irradiated azobenzene solutions with sunlight or UV-light and obtained the cis form by fractional crystallization. Chromatographic methods were also used in the preparation of cis-2,2'-azopyridine (35) [40] and the cis-2,2'-or cis-l,2'-azonaph- References,pp.67-69 35 36 37 thalenes (36 and 37, respectively) [41]; in the latter case it was necessary to carry out the experiments at 0° owing to the great tendency of the cis forms to undergo thermal re-isomerizations. The composition of the equilibrium depends on the nature and the temperature of the solvent.…”

Section: D) Azo Compoundsmentioning

confidence: 99%

Photochemical stereoisomerization

Schönberg¹

1968

Preparative Organic Photochemistry

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Spectroscopic Studies on Dyes. IV. The Fluorescence Spectra of Thioindigo Dyes¹

Cited by 48 publications

References 2 publications

Photoswitchable fluorescent diarylethene derivatives with short alkyl chain substituents

Photoswitchable fluorescent diarylethene derivatives with short alkyl chain substituents

Rewritable Near-Field Optical Recording on Photochromic Perinaphthothioindigo Thin Films: Readout by Fluorescence

Photochemical stereoisomerization

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Spectroscopic Studies on Dyes. IV. The Fluorescence Spectra of Thioindigo Dyes1

Cited by 48 publications

References 2 publications

Photoswitchable fluorescent diarylethene derivatives with short alkyl chain substituents

Photoswitchable fluorescent diarylethene derivatives with short alkyl chain substituents

Rewritable Near-Field Optical Recording on Photochromic Perinaphthothioindigo Thin Films: Readout by Fluorescence

Photochemical stereoisomerization

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Spectroscopic Studies on Dyes. IV. The Fluorescence Spectra of Thioindigo Dyes¹