Femtosecond spectroscopic study on photochromic salicylideneaniline

Mitra, Sivaprasad; Tamai, Naoto

doi:10.1016/s0009-2614(97)01279-7

Cited by 87 publications

(77 citation statements)

References 15 publications

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“…4A); secondly, the positive band with a maximum at $470 nm is assigned to the absorption from the S 0 state of the trans-keto tautomer, corresponding well to the time-dependent UV/vis absorption spectra (Fig. S5) and previous reports on photochromic Schiff base [27,28]; thirdly, the positive band with a maximum at $370 nm is possibly related to a very long-living species, i.e., the syn-enol form [3]. This possibility is further confirmed by theoretical calculation (see details and Scheme S1 in the Supporting information).…”

Section: Time-dependent Uv/vis Absorption Spectrasupporting

confidence: 82%

A photochromic thin film based on salicylideneaniline derivatives intercalated layered double hydroxide

Wang

Yan

Wei

et al. 2010

Chemical Physics Letters

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Section: Time-dependent Uv/vis Absorption Spectrasupporting

confidence: 82%

A photochromic thin film based on salicylideneaniline derivatives intercalated layered double hydroxide

Wang

Yan

Wei

et al. 2010

Chemical Physics Letters

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“…lution have been used. [33][34][35][36] In our time-resolved study, we used time-domain technique with both picosecond and femtosecond resolution. Figure 7 presents the fluorescence decay profiles of ADDSA-1 in acetonitrile at both the emission maximum.…”

Section: Is Anomalous Emission Due To An Esipt Reaction With In the Smentioning

confidence: 99%

“…Our shorter lifetime components are in good agreement with ¼ 10 AE 3 ps in acetonitrile, found by Ziolek et al for N,N 0 -bis(salicylidene)-p-phenylenediamine (BSP). 35 Recently, Vergas has reported the biexponential decay for the substituted SA compounds in cyclohexane and alcoholic solution. The shorter lifetime component is about 0.02 ns, and the longer lifetime component is about 1.5 ns.…”

Section: Is Anomalous Emission Due To An Esipt Reaction With In the Smentioning

confidence: 99%

Dual Fluorescence in a Schiff Base Derived from an Acridinedione Dye. Excited State Intramolecular Proton Transfer

Thiagarajan¹,

Ramamurthy²

2007

Bulletin of the Chemical Society of Japan

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Newly synthesized nonconjugated, but covalently linked, bichromophoric systems (ADDSA) contain a salicylideneaniline (SA) moiety linked to an acridinedione (ADD) fluorophore via a covalent bond. The absorption and fluorescence characteristics of the ADDSA systems in various solvents reveal that the dual fluorescence originates from two different chromophores in the same molecule. The solvent polarity independent, long wavelength anomalous emission originates from the keto form of SA moiety via excited state intramolecular proton transfer (ESIPT). The ESIPT pathway was further confirmed by the benzylideneaniline (BA) and ADD moieties coupled non-proton transfer model system (ADDBA). Absence of the longer wavelength anomalous emission in the steady state as well as the shorter lifetime component in the time-resolved study for ADDBA system supports ESIPT mechanism for long wavelength anomalous emission in ADDSA system. ESIPT, discovered by Weller in 1955, has been the subject of continuous interest of researchers for more than five decades. 1 Photoinduced proton transfer, which is a representative of a limited number of adiabatic photochemical processes giving rise to fluorescence with an abnormally large Stokes shift, 2 plays an important role in biophysics, 3 and has practical application in technology, for example, in organic scintillators. 4 Among the molecular systems characterised by excited state proton transfer, both efficient organic photochromes 5 and polymer ultraviolet stabilisers 6 are of much interest. Prospects for the use of ESIPT systems in luminescent solar energy concentrators have also been discussed in literature. 7 For the ESIPT reaction to occur, it is necessary that proton-donor and proton-acceptor moieties be in close proximity and conjugated to one another in an organic molecule. ESIPT is considered as the driving force for the concerted enhancement of their acidity or basicity upon the transition to an excited state. 8 If a molecule carries its own base, excited-state proton transfer can occur intramolecularly and becomes more or less independent of the surrounding solvent. ESIPT reaction is extremely fast (subpicosecond kinetics) and also occurs in rigid glasses and at very low temperatures. 9 Very often, only the ESIPT product (P Ã ) fluoresces, and this is the source of extremely large Stokes shift, which are fairly independent of medium and temperature. Thus, ESIPT dyes are ideal candidates for use as fluorescence labels in order to avoid interference from other fluorescent material present in the sample to be analyzed.Most of the publications on ESIPT deal with derivatives of salicylic acid, its esters and amides, 10 salicylaldehyde, acetophenone and related compounds, 11 o-hydroxybenzoxazoles, 12 benzothiazoles, 13 triazoles, 14 flavonols, 15 anthraquinones, 16 bipyridyls, 17 and malonic aldehyde. 18 Recently, Chou et al. have studied the solvent polarity tuned excited state, charge-transfer-coupled proton transfer reaction in p-N,N-ditolylaminosalicylaldehyde-and 3-hydroxyflavone-ba...

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“…Furthermore, various salicylideneanilines like 3a-d ( Fig. 1) have attracted considerable attention both experimentally [22][23][24] and theoretically [25,26] because of their structural simplicity, and also capable of exhibiting intramolecular proton transfer on photoexcitation towards the formation of relatively long lived photochromic product ( Fig. 2(b)).…”

Section: Introductionmentioning

confidence: 99%

The synthesis, characterization and structures of some 4-[((E)-1-{2-hydroxy-5-[(E)-2-(aryl)-1-diazenyl]phenyl}methylidene)amino]benzoic acid

et al. 2009

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Femtosecond spectroscopic study on photochromic salicylideneaniline

Cited by 87 publications

References 15 publications

A photochromic thin film based on salicylideneaniline derivatives intercalated layered double hydroxide

A photochromic thin film based on salicylideneaniline derivatives intercalated layered double hydroxide

Dual Fluorescence in a Schiff Base Derived from an Acridinedione Dye. Excited State Intramolecular Proton Transfer

The synthesis, characterization and structures of some 4-[((E)-1-{2-hydroxy-5-[(E)-2-(aryl)-1-diazenyl]phenyl}methylidene)amino]benzoic acid

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