Chemically-induced geometrical isomerization of stilbenes during peroxyoxalate chemiluminescence reaction: revisit to ‘photochemistry without light’

Motoyoshiya, Jiro; Watanabe, Kota; Takizawa, Airi; Shimizu, H.; Maruyama, Takayuki

doi:10.1016/j.tetlet.2013.11.094

Cited by 2 publications

(6 citation statements)

References 19 publications

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“…Energy transfer from the excited product to adjacent DNA pyrimidines then sensitizes dimerization and CPDs formation. In addition, chemienergetic species have been used to induce the excited-state chemistry of several other nonbiologically relevant molecules by energy transfer, among others, the cis – trans isomerization of stilbene. , Other excited-state reactions can also be of technological interest. In this context, Ermoshkin et al reported a study showing how to produce photopolymers inside tubes or behind a pipe .…”

Section: Ante Et Post Chemiexcitationmentioning

confidence: 99%

Chemi- and Bioluminescence of Cyclic Peroxides

et al. 2018

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Bioluminescence is a phenomenon that has fascinated mankind for centuries. Today the phenomenon and its sibling, chemiluminescence, have impacted society with a number of useful applications in fields like analytical chemistry and medicine, just to mention two. In this review, a molecular-orbital perspective is adopted to explain the chemistry behind chemiexcitation in both chemi- and bioluminescence. First, the uncatalyzed thermal dissociation of 1,2-dioxetane is presented and analyzed to explain, for example, the preference for triplet excited product states and increased yield with larger nonreactive substituents. The catalyzed fragmentation reaction and related details are then exemplified with substituted 1,2-dioxetanone species. In particular, the preference for singlet excited product states in that case is explained. The review also examines the diversity of specific solutions both in Nature and in artificial systems and the difficulties in identifying the emitting species and unraveling the color modulation process. The related subject of excited-state chemistry without light absorption is finally discussed. The content of this review should be an inspiration to human design of new molecular systems expressing unique light-emitting properties. An appendix describing the state-of-the-art experimental and theoretical methods used to study the phenomena serves as a complement.

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Section: Ante Et Post Chemiexcitationmentioning

confidence: 99%

Chemi- and Bioluminescence of Cyclic Peroxides

et al. 2018

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“…2,[6][7][8] Since then, chemical reactivity and transformation of excited triplet and singlet species chemically produced in the thermolysis of dioxetanes, dioxetanones, or oxalates have been used for the determination of chemiexcitation yields. 4,5,9 In addition, the chemienergetic species have been used to induce excited-state chemistry of target molecules by energy transfer. [9][10][11] Similar phenomena have been postulated to occur in biological systems catalyzed by enzymes such as peroxidases since the excited species were of the type expected from cleavage of a dioxetane/dioxetanone intermediate.…”

Section: Introductionmentioning

confidence: 99%

“…4,5 Recently, Motoyoshiya et al 9 have performed a work to study the different efficiency of the cis-trans isomerization of stilbene between the process induced by energy transfer from a peroxylate and that promoted by intra-sensitization from a molecular system in which stilbene is covalently linked to the peroxylate. However, many authors indicate that in the chemiluminescence reaction of peroxylate systems an initial decomposition of the peroxylates takes place to form dioxetanedione which is the actual chemiluminophore.…”

Section: Introductionmentioning

confidence: 99%

“…4,5,9 In addition, the chemienergetic species have been used to induce the excited-state chemistry of target molecules by energy transfer. [9][10][11] Similar phenomena have been postulated to occur in biological systems catalyzed by enzymes such as peroxidases since the excited species were of the type expected from the cleavage of a dioxetane/dioxetanone intermediate. 4,5,12 Some illustrative examples are the detection of thymine dimers in the calf thymus DNA treated with trimethyl-1,2-dioxetane without UV radiation, 13,14 the oxidative DNA damage by radicals generated via the chemiexcitation of ketones, 15 the production of the plant hormone ethylene from enzymatically generated triplet 1-butanal, 16 or the opening of the B-ring of protovitamins D through triplet sensitization in the isobutyraldehyde/peroxidase/O 2 system.…”

Section: Introductionmentioning

confidence: 99%

“…1a) has been much less exploited. 4,5 Recently, Motoyoshiya et al 9 have carried out a study comparing the efficiency of the cis-trans isomerization of stilbene induced by energy transfer from a peroxylate with that of the process promoted by intrasensitization from a molecular system in which stilbene is covalently linked to the peroxylate. Higher efficiency is reported for the latter.…”

Section: Introductionmentioning

confidence: 99%

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Theoretical study of the dark photochemistry of 1,3-butadiene via the chemiexcitation of Dewar dioxetane

Farahani

Lundberg

Lindh

et al. 2015

Phys. Chem. Chem. Phys.

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Excited-state chemistry is usually ascribed to photo-induced processes, such as fluorescence, phosphorescence, and photochemistry, or to bio-and chemiluminescence, in which light emission is originated by a chemical reaction. A third class of excited-state chemistry, however, is possible that promotes photochemical phenomena by chemienergizing certain chemical groups without light -chemiexcitation. By studying Dewar dioxetane, which can be viewed as the combination of 1,2-dioxetane and 1,3-butadiene, we show here how the isomerization * To whom correspondence should be addressed † Uppsala ‡ València ¶ UC 3 1 channel that characterizes the photo-induced chemistry of 1,3-butadiene can be reached at a later stage after the thermal decomposition of the dioxetane moiety. Multi-reference multiconfigurational quantum chemistry methods and accurate reaction-path computational strategies were used to determine the reaction coordinate that first decomposes the dioxetane, next transfers non-adiabatically the state from the ground to the excited state, and finally brings the system into the photochemical channel of the 1,3-butadiene group. With the present study, we open a new area of research within computational photochemistry to study chemically-induced excited-state chemistry that is difficult to tackle experimentally due to the short-lived character of the species involved in the process. The findings shall be of relevance to unveil "dark" photochemistry mechanisms which might operate in biological systems in conditions of lack of light to allow reactions that are typical of photo-induced phenomena.

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Chemically-induced geometrical isomerization of stilbenes during peroxyoxalate chemiluminescence reaction: revisit to ‘photochemistry without light’

Cited by 2 publications

References 19 publications

Chemi- and Bioluminescence of Cyclic Peroxides

Chemi- and Bioluminescence of Cyclic Peroxides

Theoretical study of the dark photochemistry of 1,3-butadiene via the chemiexcitation of Dewar dioxetane

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