An insight into the solvent effect on photo-, solvato-chromism of spiropyran through the perspective of intermolecular interactions

Tian, Wenwen; Tian, Jing

doi:10.1016/j.dyepig.2014.01.020

Cited by 111 publications

(82 citation statements)

References 34 publications

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“…Spiropyran (SP) systems are well-known chromophores that reversibly photoisomerize to the conjugated merocyanine (MC) moieties, [1][2][3][4] which are attractive candidates for designing devices for optical switching and storage, sensors, cell imaging, etc. [5][6][7][8][9] SP absorbs light in the wavelength range of 200-400 nm to induce bond-cleavage producing the open form MC (Fig.…”

Section: Introductionmentioning

confidence: 99%

Energetic and structural properties of different conformations of merocyanine and its protonated forms

Singh

Böhm

Balasubramanian

2015

Chemical Physics Letters

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We investigate the conformational stabilities, dipole moments, bond lengths and partial charges of photo-sensitive spiropyran (1′,3′-dihydro-1′,3′,3′-trimethyl-6-nitro-spiro[2H-1-benzopyran-2,2′-[2H]indole]) after its photo-switching to the open form conformers, merocyanine and its protonated counterparts. Two approaches, an ab initio Hartree-Fock method supplemented by the Møller-Plesset second-order perturbation theory and density functional theory under B3LYP parameterization, are employed with extended basis sets to examine the energetic ordering of the conformers in vacuum and in an aqueous environment. The influence of the solvent on the conformers is demonstrated by the notable changes in the structural and electrostatic properties.

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Section: Introductionmentioning

confidence: 99%

Energetic and structural properties of different conformations of merocyanine and its protonated forms

Singh

Böhm

Balasubramanian

2015

Chemical Physics Letters

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“…According to the definition of negative photochromism [72,73], CMCH-g-MCA is a negative photochromic dye. To the best of our knowledge, the negative photochromism of polymers linked covalently with spirooxazine groups has not been reported [72].…”

Section: Photochromic Propertiesmentioning

confidence: 99%

Preparation and analysis of photochromic behavior of carboxymethyl chitin derivatives containing spiropyran moieties

Sun

Yao

et al. 2020

Designed Monomers and Polymers

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1ʹ-(2-Acryloxyethyl)-3,3ʹ-dimethyl-6-nitrospiro[2 H-1-benzopyran-2,2ʹ-indoline] (SPA) was synthesized and grafted onto a water-soluble carboxymethyl chitin (CMCH) macromolecule to prepare a photochromic copolymer (CMCH-g-SPA). The structure of CMCH-g-SPA was characterized by Fourier-transform infrared (FT-IR) spectroscopy, thermogravimetric (TG) analysis, X-ray diffraction (XRD) analysis, water-solubility evaluation, and UV-vis spectroscopy. XRD patterns of CMCH-g-SPA revealed that grafting copolymerization disrupts the CMCH semicrystalline structure, thus improving water solubility. UV-vis spectroscopy results supported the negative photochromic behavior of the merocyanine (MC) form of CMCH-g-SPA (CMCH-g-MCA) present in a water solution of the target copolymer. In addition to high solvent polarity, the intermolecular and intramolecular electrostatic attraction between the indolenine cation and the COO − anion were found to be influencing factors, which stabilize these MC form of spiropyran groups grafted onto CMCH. In a water solution, visible light bleaching was completed over a short period (8 minutes) under artificial visible light irradiation and the thermal coloration reaction, whose rate constant at 25 °C was 4.64 × 10 −4 s −1 , which fit the first-order reaction equation. After ten photochromic cycles in water solution, the relative absorption intensity of CMCH-g-MCA decreased by 7.92%.

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“…DermolekulareSchalterSpiropyran/Merocyaninist ausande-renA rbeiteni nd er fachwissenschaftlichenu nd fachdidakti-schenF orschung hinlänglich bekannt [4][5][6][7][8][9][10][11][12][13]. DurchB estrahlung mitLicht verschiedenerW ellenlängen kçnnen diefarblose SpeziesS piropyran( SP)u nd dasf arbige Isomer Merocyanin( ME)r eversibelg eschaltet werden (Abb.1).…”

Section: Spiropyran/merocyaninals Molekularer Schalterunclassified

Chem4Digit – Chemistry for Digital Logics

Spinnen

Tausch

2018

Chemkon

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Zusammenfassung: UnterB erücksichtigung derG esetzmäßigkeitenp hotochemischer Prozesse undd urch ge-schicktesDesignvon Bauelementen kçnnen optische undchemische Signalegemäßder Booleschen Aussagenlogikkombiniertwerden, indemman molekulare Schalter nutzt. PhotochromefunktionelleF arbstoffekçnnten so beispielsweise in derMedizinund in neuenMaterialien Anwendungfinden.Stichworte: BinärerZ ahlencode·BoolescheA lgebra·Fluoreszenz·Photochromie ·U ND-Verknüpfung· INHIBIT-Ve rknüpfung·voll-optische Logik-Schaltung Chem4Digit -C hemistry forDigital LogicsAbstract: Followingthe principles of photochemicalprocesses anddesigning clever devices, opticaland chemicalinputscan be combined accordingtothe propositionallogicsofBoolean algebrausing molecularswitches. Doings o, photochromic functional dyes couldf ound application, fore xample in medicine andi nnew materials.

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An insight into the solvent effect on photo-, solvato-chromism of spiropyran through the perspective of intermolecular interactions

Cited by 111 publications

References 34 publications

Energetic and structural properties of different conformations of merocyanine and its protonated forms

Energetic and structural properties of different conformations of merocyanine and its protonated forms

Preparation and analysis of photochromic behavior of carboxymethyl chitin derivatives containing spiropyran moieties

Chem4Digit – Chemistry for Digital Logics

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