Photochromism of cationic spiropyran-doped silica gels

Léaustic, Anne; Dupont, Agnès; Yu, Peng; Clément, René

doi:10.1039/b104456g

Cited by 24 publications

(19 citation statements)

References 13 publications

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“…Then, other iodides, (R-SP) + I − (R = i-Pr, Ph, nhexyl, C 2 H 4 OH) with the same properties [9,10] were synthesized.…”

Section: )-N(sp 3 ) Bond Lengths Inmentioning

confidence: 99%

Spiropyran salts and their neutral precursors: synthesis, crystal structure, photochromic transformations in solutions and solid state

Yurieva¹,

Алдошин²

2015

Organic Photonics and Photovoltaics

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This review covers investigations of spiropyran iodides with N-substituted indoline fragment, and with the pyran cycle being annelated to N-methylated pyridine ring. The schemes of synthesis of iodides and their neutral precursors, as well as results of X-ray analysis and photochemical study of the crystals of the obtained compounds are presented. Based on our and literature data, the relationship between the structure and photochromic properties has been discussed for a series of salts and neutral pyridospiropyrans.

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“…Then, other iodides, (R-SP) + I − (R = i-Pr, Ph, nhexyl, C 2 H 4 OH) with the same properties [9,10] were synthesized.…”

Section: )-N(sp 3 ) Bond Lengths Inmentioning

confidence: 99%

Spiropyran salts and their neutral precursors: synthesis, crystal structure, photochromic transformations in solutions and solid state

Yurieva¹,

Алдошин²

2015

Organic Photonics and Photovoltaics

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“…В результате ранее выполненных исследований показана возможность получения фотохромных систем с обратным фотохромизмом на основе дендримерных наночастиц диоксида кремния и нитро- [2,3], а также гидроксизамещенных индолиновых спиропиранов [4,5]. Обратный фотохромизм наночастиц диоксида кремния обнаружен и при использовании катионных спиропиранов [6]. Положительный фотохромизм на поверхности этих наночастиц проявляют нитрозамещенные спиропираны с длинным метиленовым заместителем при атоме азота индолинового фрагмента [7].…”

Section: Introductionunclassified

Спектральные Проявления Взаимодействия Наночастиц Диоксида Кремния С Молекулами Фотохромных Соединений

Барачевский¹,

Кобелева²,

Горелик³

et al. 2018

Журнал Технической Физики

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Проведено сравнительное спектрально-кинетическое исследование водно-этанольных фотохромных систем, содержащих фотохромные соединения из класса спиропиранов, спирооксазинов, хроменов и диарилэтенов без и в присутствии наночастиц диоксида кремния. Установлено, что в завимости от структуры соединения молекулы могут вступать в химическое или физическое взаимодействие с поверхностью наночастиц.

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“…Likewise, their respective singlet cationic counterparts have been shown to display photochromism in both solution 6,7 and crystalline state. 8,9 These have been employed in a variety of applications. For example, salts of spiropyrans have been used for the development of hybrid multi-functional materials, in which the spiropyran acts as a photochemical molecular switch perturbing the magnetic properties of the crystal lattice.…”

Section: Introductionmentioning

confidence: 99%

“…[11][12][13] Although the thermal reversibility of this transformation has been exploited extensively in applications, thermally stable MC isomers have been attained in solution, as shown by Minkin and coworkers 7 through the addition of cationic substituents, by Kortekaas et al through protonation of the pyran oxygen atoms of bis-spiropyrans, 14 and in the solid state when embedded in a silica gel. 9 Although the photochromism of spiropyrans has been known for over half a century, their electrochromism has received detailed attention only recently. Ivashenko et al 15 demonstrated that oxidatively driven ring-opening of the nitro-spiropyran compound 1 shown in Scheme 2(a) does not occur, but instead the indole moiety undergoes rapid aryl-aryl dimerisation upon oxidation by a mechanism analogous to the dimerisation of N,N-dimethylaniline (DMA) to N,N,N,N-tetramethylbenzidine (TMB).…”

Section: Introductionmentioning

confidence: 99%

Accidental degeneracy in the spiropyran radical cation: charge transfer between two orthogonal rings inducing ultra-efficient reactivity

Mendive-Tapia

Kortekaas

Steen

et al. 2016

Phys. Chem. Chem. Phys.

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Photochromism of the spiropyran radical cation to the corresponding merocyanine form is investigated by a combination of electrochemical oxidation, UV/vis absorption spectroscopy, spectroelectrochemistry and first-principles calculations (TD-DFT, CAS-SCF and CAS-PT2). First, we demonstrate that the ring-opening of mono-spiropyrans occurs upon one-electron oxidation and that it can be driven photochemically as well as thermally, with trapping of the merocyanine by protonation. Second, in order to explain this experimentally observed spectroelectrochemical behaviour we suggest a theoretical mechanism based on the reactivity of the two lowest electronic excited-states, which promotes effective electron transfer from the indoline (nitrogen-ring) to the pyran (oxygen-ring) moieties (and vice versa) through a conical intersection seam of degeneracy. Characterisation of the minimum energy conical intersection on this crossing revealed that it presents a rare diabatic trapping topology. The excited state molecule cannot escape from crossing the intersection seam due to the presence of only one degeneracy-lifting coordinate that efficiently channels into the formation of the merocyanine photoproduct, so giving rise to a "kitchen sink" funnel-like effect. Therefore, assuming rapid relaxation after vertical excitation to a higher electronic state, photoconversion cannot be avoided in the D electronic state, which rationalises the remarkably efficient visible light driven excited-state reactivity observed experimentally.

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Photochromism of cationic spiropyran-doped silica gels

Cited by 24 publications

References 13 publications

Spiropyran salts and their neutral precursors: synthesis, crystal structure, photochromic transformations in solutions and solid state

Spiropyran salts and their neutral precursors: synthesis, crystal structure, photochromic transformations in solutions and solid state

Спектральные Проявления Взаимодействия Наночастиц Диоксида Кремния С Молекулами Фотохромных Соединений

Accidental degeneracy in the spiropyran radical cation: charge transfer between two orthogonal rings inducing ultra-efficient reactivity

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