Some Photochemical Transformations of Polyenic Compounds

M, Mousseron

doi:10.1002/9780470133347.ch7

Cited by 9 publications

(2 citation statements)

References 42 publications

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“…The ionone framework anchors molecule such as retinal into opsin protein allowing rest of the molecule to be flexible enough to undergo selective isomerization that serves to trigger a biological function such as "vision." Because of its biological relevance, b-ionone and its higher members such as retinal have received considerable attention of photochemists and photophysicists, and synthetic, theoretical, and biochemists as well as spectroscopists (15)(16)(17)(18)(19)(20)(21)(22)(23)(24). Of the various possible geometric isomers, 7-cis-isomers are most hindered and their synthesis has been a challenge (25)(26)(27)(28)(29).…”

Section: Introductionmentioning

confidence: 99%

An Organic Capsule as a Matrix to Capture and Store Reactive Molecules at Room Temperature in Aqueous Solution: 7‐cis‐β‐Ionone^†

Sunny

Ramamurthy

2021

Photochem & Photobiology

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Low-temperature m atrix isolation method is the most popular one to generate and store reactive molecules and characterize them by in situ IR spectroscopy. Recognizing the need for a simpler method to trap and store such molecules and characterize by NMR spectroscopy at room temperature in solution, we have performed experiments exploring the value of water-soluble octa acid (OA) capsule as a storage vessel. The molecule we have chosen to illustrate the feasibility is the highly hindered 7-cis-b-ionone, which has been established to exist in equilibrium with its cyclic form with the later favored at room temperature. In this study, we have shown that confined space can be an alternative to temperature to tilt an equilibrium toward higher energy isomer. During the course of the study, we were surprised to note that 7trans-b-ionone aggregates in water and has distinct 1 H NMR spectra. Ability to assemble characterizable organic aggregates in water reveals the value of water as a reaction medium that is yet to be fully explored by photochemists. Finally, we have clarified the likely mechanism of secondary photoreaction of a-pyran to the final photoproduct that involves 1,5hydrogen migration.

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Section: Introductionmentioning

confidence: 99%

An Organic Capsule as a Matrix to Capture and Store Reactive Molecules at Room Temperature in Aqueous Solution: 7‐cis‐β‐Ionone^†

Sunny

Ramamurthy

2021

Photochem & Photobiology

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“…The deactivation of olefin‐excited states results in E – Z isomerization, sigmatropic shifts and electrocyclization reactions (1–3). The photochemical E – Z isomerization in olefins is a well‐studied process (4–8).…”

Section: Introductionmentioning

confidence: 99%

Ionic Photodissociation in Arylallyl Acetates¶

Srinivas

Reddy

et al. 2007

Photochemistry and Photobiology

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We have synthesized several 3‐arylallyl acetates 1, 2, 3, 5 and 6, and E‐3‐(1‐naphthyl)‐2‐propene‐1‐ol 4 for studying ionic photodissociation. Compounds 1, 2 and 3 underwent an efficient ionic photodissociation in polar solvents like acetonitrile and methanol leading to the formation of rearranged acetate and methyl ether products, as well as undergoing an E–Z isomerization. The arylallyl alcohol 4 and the two arylallyl acetates 5 and 6 did not undergo ionic photodissociation. Quantum yields of product formation, quantum yields of fluorescence, solvent polarity effects and triplet‐sensitization studies indicated that a highly polarized excited singlet state is responsible for the ionic photodissociation. Both the singlet‐ and triplet‐excited states are effective in displaying E–Z isomerization in 1, 2, 3 and 4. Compounds 5 and 6 are highly fluorescent, and the fluorescence may be the excited state deactivation pathway along with internal conversion.

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Photopericyclic Reactions of Conjugated Dienes and Trienes

Cook

Leigh

2009

Patai's Chemistry of Functional Groups

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Introduction Ground State Conformational Equilibria and E , Z ‐Isomerization The Excited Singlet States of Conjugated Polyenes: UV Absorption and Emission Spectra Singlet State Photochemistry of Conjugated Dienes and Trienes Conclusion

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Some Photochemical Transformations of Polyenic Compounds

Cited by 9 publications

References 42 publications

An Organic Capsule as a Matrix to Capture and Store Reactive Molecules at Room Temperature in Aqueous Solution: 7‐cis‐β‐Ionone^†

An Organic Capsule as a Matrix to Capture and Store Reactive Molecules at Room Temperature in Aqueous Solution: 7‐cis‐β‐Ionone^†

Ionic Photodissociation in Arylallyl Acetates¶

Photopericyclic Reactions of Conjugated Dienes and Trienes

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Some Photochemical Transformations of Polyenic Compounds

Cited by 9 publications

References 42 publications

An Organic Capsule as a Matrix to Capture and Store Reactive Molecules at Room Temperature in Aqueous Solution: 7‐cis‐β‐Ionone†

An Organic Capsule as a Matrix to Capture and Store Reactive Molecules at Room Temperature in Aqueous Solution: 7‐cis‐β‐Ionone†

Ionic Photodissociation in Arylallyl Acetates¶

Photopericyclic Reactions of Conjugated Dienes and Trienes

Contact Info

Product

Resources

About

An Organic Capsule as a Matrix to Capture and Store Reactive Molecules at Room Temperature in Aqueous Solution: 7‐cis‐β‐Ionone^†

An Organic Capsule as a Matrix to Capture and Store Reactive Molecules at Room Temperature in Aqueous Solution: 7‐cis‐β‐Ionone^†