A Water-Stable Quadricyclane Derivative

Tamiaki, Hitoshi; Maruyama, Kazuhiro

doi:10.1246/cl.1988.1875

Cited by 6 publications

(2 citation statements)

References 7 publications

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“…If the use of the norbornadiene/quadricyclane as energy storage systems is to be exploited, systems have to be devised that can be cyclized using sunlight. This is the case with the water-soluble norbornadiene (469) that is efficiently converted into the corresponding quadricyclane on irradiation with sunlight 296 . Other norbornadienes with carboxylic acid functional groups (e.g.…”

Section: E Other Cycloadditionsmentioning

confidence: 99%

Photochemistry of Cyclobutanes: Synthesis and Reactivity

Horspool

2009

Patai's Chemistry of Functional Groups

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Introduction Cycloaddition Reactions Involving Alkenes Cycloaddition Reactions Involving Dienes and Trienes Cycloadditions of Enones and Related Compounds Photochemistry of Ketones Cage Compounds Cyclobutane Ring Opening Reactions

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Section: E Other Cycloadditionsmentioning

confidence: 99%

Photochemistry of Cyclobutanes: Synthesis and Reactivity

Horspool

2009

Patai's Chemistry of Functional Groups

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“…Almost all of the MOST systems tested so far have been designed to work in organic solvents and only a very few to be used in water [34,35,[45][46][47][48][49][50], although the aqueous medium should be preferable for environmental sustainability. This is probably due to early observations of possible QC reactivity with water in the absence and in the presence of metal catalysts [45,[51][52][53], despite stable and successful MOST functioning in water also being obtained [34,35,[45][46][47][48][49][50].…”

Section: Introductionmentioning

confidence: 99%

A Norbornadiene-Based Molecular System for the Storage of Solar–Thermal Energy in an Aqueous Solution: Study of the Heat-Release Process Triggered by a Co(II)-Complex

Castro,

Gancheff,

Ramos

et al. 2023

Molecules

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It is urgent yet challenging to develop new environmentally friendly and cost-effective sources of energy. Molecular solar thermal (MOST) systems for energy capture and storage are a promising option. With this in mind, we have prepared a new water-soluble (pH > 6) norbornadiene derivative (HNBD1) whose MOST properties are reported here. HNBD1 shows a better matching to the solar spectrum compared to unmodified norbornadiene, with an onset absorbance of λonset = 364 nm. The corresponding quadricyclane photoisomer (HQC1) is quantitatively generated through the light irradiation of HNBD1. In an alkaline aqueous solution, the MOST system consists of the NBD1−/QC1− pair of deprotonated species. QC1− is very stable toward thermal back-conversion to NBD1−; it is absolutely stable at 298 K for three months and shows a marked resistance to temperature increase (half-life t½ = 587 h at 371 K). Yet, it rapidly (t½ = 11 min) releases the stored energy in the presence of the Co(II) porphyrin catalyst Co-TPPC (ΔHstorage = 65(2) kJ∙mol−1). Under the explored conditions, Co-TPPC maintains its catalytic activity for at least 200 turnovers. These results are very promising for the creation of MOST systems that work in water, a very interesting solvent for environmental sustainability, and offer a strong incentive to continue research towards this goal.

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