Novel Fatigue-Resistant Spirooxazines

Метелица, А. В.; Knyazhansky, M. I.; Palchkov, V. A.; Zubkov, Oleg A.; Vdovenko, A. V.; Shelepin, N. E.

doi:10.1080/10587259408037783

Cited by 3 publications

(2 citation statements)

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“…The electronic absorption spectrum of SPO 204 of the phenanthrene series has an additional maximum at 375 nm (toluene) compared to the absorption spectrum naphtho derivative 1, which is the manifestation of the vibrational nature of the long-wavelength absorption band belonging to the modified phenanthrene system. 174 This effect is even more pronounced in the case of anthracene derivative 103. The spectrum of the latter compound has an additional long-wavelength vibrational maximum at 427 nm (heptane).…”

Section: Spectral Properties Of Spirooxazines 1 Electronic Absorption...mentioning

confidence: 95%

Spirooxazines: synthesis, structure, spectral and photochromic properties

Lokshin¹,

Samat²,

Метелица³

2002

Russ. Chem. Rev.

172

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Section: Spectral Properties Of Spirooxazines 1 Electronic Absorption...mentioning

confidence: 95%

Spirooxazines: synthesis, structure, spectral and photochromic properties

Lokshin¹,

Samat²,

Метелица³

2002

Russ. Chem. Rev.

172

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“…Synthesis of SO. Compounds SO 1 −SO 3 and SO 7 −SO 9 (see Table for structures) were prepared as described elsewhere by coupling 9-amino-10-hydroxyphenanthrene hydrochloride (for SO 1 −SO 3 ), 9-amino-10-hydroxy-2-nitrophenanthrene hydrochloride (for SO 7 and SO 9 ), and 9-amino-10-hydroxy-4-nitrophenanthrene hydrochloride (for SO 8 ) with substituted 2,3,3-trimethyl-3 H -indolium iodides. Compounds SO 4 −SO 6 were prepared by coupling 6-hydroxy-5-nitroso-1,7-phenanthroline (for SO 4 ) and 6-hydroxy-5-nitroso-1,10-phenanthroline (for SO 5 and SO 6 ) with substituted 2,3,3-trimethyl-3 H -indolium iodides.…”

Section: Methodsmentioning

confidence: 99%

Photochromism of Spirooxazines in Homogeneous Solution and Phospholipid Liposomes

et al. 1998

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The photochromic behavior of several spirooxazines (SO) containing phenanthrene or phenanthroline moieties in the oxazine part of molecules has been investigated in several solvents and phosphatidylcholine (PC) liposomes. The solvatochromic properties of the merocyanine (MC) forms of these dyes were used to probe their location within the PC membrane. Transient spectroscopic measurements revealed that, when first formed by photoexcitation, the MC forms of phenanthroline-containing spirooxazines were located at relatively nonpolar sites within the membrane, but they subsequently moved to a more polar environment typical of the aqueous-organic interface. The characteristic time for this intersite movement was τ ≈ 10 -3 s, corresponding to a diffusion coefficient of D ≈ 10 -11 cm 2 s -1 . In contrast, these spectral shifts were not observed when PC liposome-bound SO containing the phenanthrene moiety were photoexcited, suggesting that either intersite diffusion was more rapid for these compounds or the initially formed MC (and its spiro precursor) were located in a more polar microenvironment. The rate of thermal ring-closing following UV photoexcitation decreased modestly when either an electron-withdrawing group was present on the MC oxazine ring or an electrondonating group was present on the MC indoline ring. A dramatic increase in the ring-closing rate was observed for an o-phenanthroline-containing SO coordinated to a Ru(bpy) 2 2+ metal center, an effect attributable to strong donation of electron density from the Ru(II) d-orbitals into the ligand π*-orbitals.

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