The Photochemistry and Photophysics of Spiropyrans

Kholmanskii, A. S.; Dyumaev, K. M.

doi:10.1070/rc1987v056n02abeh003262

Cited by 66 publications

(61 citation statements)

References 64 publications

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“…Spiropyrans are the most widespread class of organic photochromes, the proposed mechanism [131] of photocoloration of which has not been finally established. Nevertheless, it was shown on the basis of analysis of the structure and the photochromic characteristics of indoline spiropyrans that their photochromic characteristics, due to electrocyclic cleavage of the C spiro -O bond with photoexcitation, are largely predetermined already by the fact that in the ground state this bond is elongated and weakened on account of orbital interactions between the unshared electron pair of the indoline nitrogen and the antibonding orbital of the C spiro -O bond [132][133][134].…”

Section: Photochromic Characteristics Of Spiropyransmentioning

confidence: 99%

Spiropyrans: Synthesis, Properties, and Application. (Review)

Lukyanov

Lukyanova

2005

Chem Heterocycl Compd

207

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Published data on the synthesis and structural modification of spiropyrans and bisspiropyrans and production of the heteroanalogs of spiropyrans are classified and analyzed. The chemical characteristics of spiropyrans, including complexation of the open-chain isomers and cyclic forms are examined. Special attention is paid to the photochromic characteristics of spiropyrans at interfaces between phases.

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Section: Photochromic Characteristics Of Spiropyransmentioning

confidence: 99%

Spiropyrans: Synthesis, Properties, and Application. (Review)

Lukyanov

Lukyanova

2005

Chem Heterocycl Compd

207

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“…[6][7][8] Nitrospiropyrans are members of one of the most common families of photochromic compounds. [9][10][11][12][13] They switch from a colorless to a colored state under ultraviolet irradiation and revert back to the original species in the dark. Their photochemical behavior and synthetic accessibility have already encouraged the integration of these compounds in a diversity of photoresponsive materials.…”

Section: Introductionmentioning

confidence: 99%

Photochromic Oxazines with Extended Conjugation

et al. 2009

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We synthesized four compounds with indole and benzooxazine fragments fused in their molecular skeleton and differing in the substituent in the para position, relative to the oxygen atom, of their phenoxy chromophore. This particular substituent extends the conjugation of the phenoxy chromophore and shifts its absorption bathochromically by up to 60 nm, relative to a parent compound with a 4-nitrophenoxy group. The 1,3-oxazine ring of all compounds opens upon addition of base to generate a hemiaminal incorporating a phenolate chromophore. Once again, the substituents on this fragment shift its absorption bathochromically by up to 60 nm, relative to the parent compound. Upon laser excitation at a wavelength within the absorption range of the phenoxy chromophore, the 1,3-oxazine ring of the compound incorporating a 4-nitrophenyl substituent opens in less than 6 ns to generate a zwitterionic isomer with a quantum yield of 0.11 in acetonitrile. Under these conditions, the photogenerated isomer has

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“…Nitrospiropyrans are members of one of the most common families of photochromic compounds and have been successfully incorporated within polymeric assemblies 9–13. These molecules switch from a colorless state to a colored form upon UV irradiation, after the cleavage of a [CO] bond at their spirocenter followed by the cis to trans isomerization of an adjacent [CC] bond.…”

Section: Introductionmentioning

confidence: 99%

Photochromic Polymers Based on the Photoinduced Opening and Thermal Closing of [1,3]Oxazine Rings

Tomasulo

Deni̇z

Benelli³

et al. 2009

Adv Funct Materials

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Two macromolecular constructs incorporating a single polymer backbone with multiple photochromic side chains are developed. Both systems are prepared from preformed photochromic [1,3]oxazines after the ring‐opening polymerization of their norbornene appendages. In solution, UV illumination of these polymers opens the [1,3]oxazine rings in their side chains in less than 6 ns and with a quantum yield of 0.09 in both instances. The photogenerated species incorporate a 4‐nitrophenolate chromophore, and hence, their formation is accompanied by the appearance of an intense band in the visible region of the absorption spectrum. The photoproducts revert spontaneously to the original state with first‐order kinetics in microseconds. Furthermore, both photochromic polymers tolerate hundreds of switching cycles with no sign of degradation, even in the presence of molecular oxygen. Thus, this design logic and choice of functional building blocks can translate into the realization of innovative photoresponsive materials with excellent photochromic performance.

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The Photochemistry and Photophysics of Spiropyrans

Cited by 66 publications

References 64 publications

Spiropyrans: Synthesis, Properties, and Application. (Review)

Spiropyrans: Synthesis, Properties, and Application. (Review)

Photochromic Oxazines with Extended Conjugation

Photochromic Polymers Based on the Photoinduced Opening and Thermal Closing of [1,3]Oxazine Rings

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