Inclusion Complex of Spironaphthoxazine with γ-Cyclodextrin and Its Photochromism Study

Zhang, Shu-Xiao; Fan, Meigong; Liu, Yuan-Yuan; Ma, Ying; Zhang, Guangjin; Yao, Jiannian

doi:10.1021/la700252u

Cited by 19 publications

(24 citation statements)

References 34 publications

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“…10−14 According to Zhang et al, SP-CD complexes made via the precipitation method used in this study have 1:1 guest:host stoichiometries. 12 This procedure relies on the hydrophobic SP being attracted into the hydrophobic CD cavity when added to ethanol:water solution. SP has suitable dimensions (W × L ≈ 6.5 × 13 Å) for favorable noncovalent bonding interactions with the CD cavity (ϕ × L ≈ 7.5−8.3 × 7.9 Å), 11 although some portion of the SP molecule will protrude from the cavity.…”

Section: Resultsmentioning

confidence: 99%

Electron Injection and Energy-Transfer Properties of Spiropyran–Cyclodextrin Complexes Coated onto Metal Oxide Nanoparticles: Toward Photochromic Light Harvesting

Dryza

Bieske

2015

J. Phys. Chem. C

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The photochromic and spectroscopic properties of spiropyran−γ-cyclodextrin inclusion complexes coated onto the surface of zirconia and titania nanoparticles (NPs) are examined. After ultraviolet (UV) irradiation, the colorless spiropyran (SP) isomer contained within the cyclodextrin (CD) is converted to the colored merocyanine (MC) isomer, which absorbs light in the 400−600 nm region. A significant increase in the excited-state lifetime for MC-CD on zirconia NPs (τ MC = 1.32 ns) is observed compared to MC in solution (τ MC = 0.21 ns), indicating that MC → SP photoisomerisation is hindered by the surrounding CD. Excitation of MC-CD on titania NPs results in electron injection into the titania conduction band with a quantum yield of 0.70. Excitation of MC-CD on zirconia NPs when a squaraine-based dye sensitizer is also attached to the NP surface results in energy transfer to the dye sensitizer with a quantum yield of 0.65. The prolonged excited-state lifetime of the encapsulated MC-CD is responsible for the high electron injection and energy-transfer quantum yields. The SP-CD/MC-CD system has potential applications for photochromic, light-harvesting electrodes in dye-sensitized solar cells.

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Section: Resultsmentioning

confidence: 99%

Electron Injection and Energy-Transfer Properties of Spiropyran–Cyclodextrin Complexes Coated onto Metal Oxide Nanoparticles: Toward Photochromic Light Harvesting

Dryza

Bieske

2015

J. Phys. Chem. C

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“…Where A is the optical density at λ max , B 1 and B 2 are the contributions to the initial optical density, k 1 and k 2 are rate constants of the fast and slow components and C is the fade when time approaches to infinity. 2,12 …”

Section: Resultsmentioning

confidence: 99%

“…11,13 A way to retain or adapt the physical-chemical properties of the spiropyrans can be by its molecular encapsulation in an appropriate matrix, 14 by chemical structural modification or non-covalently doping of the molecule into appropriate matrices such as polymers 15–17 or cyclodextrin (CD) cavity. 5,12 …”

Section: Introductionmentioning

confidence: 99%

Photo-response behavior of electrospun nanofibers based on spiropyran-cyclodextrin modified polymer

Sousa

Guerreiro

et al. 2010

J. Mater. Chem.

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Tunable and durable photochromic materials are a rapidly expanding area of interest, with applications ranging from biomedical devices to industrial-fields. Here we examine electrospun poly (methacrylic acid) PMAA nanofibers covalently modified with the highly photochromic molecule, spiropyran (SP) or a derivate SP which is firstly coupled to a cyclodextrin molecule (βCDSP). The photochromic properties of the starting materials and of the nanofibers were investigated. βCDSP, PMAASP and PMAA-βCDSP polymers exhibited a reverse photochromism. The kinetic results revealed a faster isomerization process for the βCDSP molecule, than that for the PMAA-βCDSP and for the PMAASP, the slowest one. The fastest isomerization is attributed to the presence of a large number of hydroxyl groups of the βCD which stabilizes the merocyanine form via hydrogen bonding, and the slowest isomerization is related to the PMAA chain structure that stabilizes the spiropyran form. Thus, combining the PMAA and βCD properties the photo-isomerization can be modulated. The photoreversibility of this material was verified by UV-visible measurements cycling visible and UV light. Infrared spectroscopy and water contact angle were used for the nanofiber surface characterization, demonstrating the presence of the spiropyran on the mats surface and also showing a minimal effect on nanofiber size and shape when compared to PMAA fiber.

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“…Solutions (250 L, 2 M) of DR1 and SP in ethanol were injected separately into 5 mL of aqueous -CDP ( 2 mol -CD/L) solution at 30 ∘ C with sonication for 10 min [45,46]. Aer 24 h of stirring, the DR1/ -CDP and SP/ -CDP inclusion complexes were deposited separately by spin coating onto ITO (indium tin oxide) glass plates and dried at 40 ∘ C in vacuo overnight for Ultraviolet/Visible (UV/VIS, Hitachi U-3900) analysis.…”

Section: Preparation Of Inclusion Complexes N-ethyl-n-(2-mentioning

confidence: 99%

Preparation of the Inclusion Complex-Type Nonlinear Optical Polymer

Wang

Chen

2013

Journal of Spectroscopy

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is study uses the inclusion complex method to import nonlinear optical (NLO) chromophores, disperse red1 (DR1), and spiropyran (SP), into the -CD cavity of the -cyclodextrin polymer ( -CDP) to prepare orderly aligned nonphotocontrollable and photocontrollable nonlinear optical polymers. Calculations support the ultraviolet/visible analyses and suggest the formation of the 1 : 2 DR1/ -CDP and 1 : 2 SP/ -CDP inclusion complexes. Upon complexation, the DR1 and SP molecules are free to align themselves along an applied electric �eld and show high order parameters of approximately 0.48 and 0.20, respectively. Reversible photochromic reactions exhibit that the SP/ -CDP complex still retains the photochromic properties following corona poling.

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Inclusion Complex of Spironaphthoxazine with γ-Cyclodextrin and Its Photochromism Study

Cited by 19 publications

References 34 publications

Electron Injection and Energy-Transfer Properties of Spiropyran–Cyclodextrin Complexes Coated onto Metal Oxide Nanoparticles: Toward Photochromic Light Harvesting

Electron Injection and Energy-Transfer Properties of Spiropyran–Cyclodextrin Complexes Coated onto Metal Oxide Nanoparticles: Toward Photochromic Light Harvesting

Photo-response behavior of electrospun nanofibers based on spiropyran-cyclodextrin modified polymer

Preparation of the Inclusion Complex-Type Nonlinear Optical Polymer

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