Adamantylideneadamantane peroxide, a stable 1,2-dioxetane.

Wieringa, J. H.; Strating, J.; Wynberg, Hans; Adam, Waldemar

doi:10.1016/s0040-4039(01)84269-6

Cited by 124 publications

(45 citation statements)

References 14 publications

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“…Decomposition of 1,2-dioxetanes is a highly exothermic process, releasing enough energy to allow the generation of products in electronically excited, emissive states (17,18). Although many 1,2-dioxetanes have vanishingly short lifetimes at room temperature, substituents such as adamantyls have been found to confer remarkable stability (16,19) and have permitted the synthesis of stable 1,2-dioxetanes that can be activated by enzymes (20)(21)(22). AMPPD [abbreviation derived from a nonsystematic name, 3-(2'-spiroadamantane)4methoxy4-(3"-phosphoryloxy)phenyl-1,2-dioxetane, disodium salt] is a stable 1,2-dioxetane with a half-life of 1 year in aqueous solution (23).…”

mentioning

confidence: 99%

Imaging of DNA sequences with chemiluminescence.

Tizard

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Ramachandran

et al. 1990

Proc. Natl. Acad. Sci. U.S.A.

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confidence: 99%

Imaging of DNA sequences with chemiluminescence.

Tizard

Cate

Ramachandran

et al. 1990

Proc. Natl. Acad. Sci. U.S.A.

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“…The strained, central four-membered dioxetane ring is known to decompose at elevated temperatures into two ketones, one of which can take an excited state and relax with the emission of a photon, producing the signature bright blue chemiluminescence. Amongst the 1,2-dioxetane family, the bis(adamantyl) derivative is striking for its stability, with an energy barrier to decomposition of 35 kcal/mol and a half-life at room temperature of around 40 years [26], largely because of the steric lock posed by the two adamantyl groups. In 2012, it was shown that the chemiluminescent cycloreversion of this dioxetane could be activated mechanically, giving mechanoluminescence (Fig.…”

Section: Mechanoluminescencementioning

confidence: 99%

Mechanochemical Reactions Reporting and Repairing Bond Scission in Polymers

Clough

Balan

Sijbesma

2015

Topics in Current Chemistry

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The past 10 years have seen a resurgence of interest in the field of polymer mechanochemistry. Whilst the destructive effects of mechanical force on polymer chains have been known for decades, it was only recently that researchers tapped into these forces to realize more useful chemical transformations. The current review discusses the strategic incorporation of weak covalent bonds in polymers to create materials with stress-sensing and damage-repairing properties. Firstly, the development of mechanochromism and mechanoluminescence as stress reporters is considered. The second half focuses on the net formation of covalent bonds as a response to mechanical force, via mechanocatalysis and mechanically unmasked chemical reactivity, and concludes with perspectives for the field.

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“…[82]. A perepoxide intermediate was reported to be trapped in the epoxide form [83] in the reaction of adamantylideneadamantane with singlet oxygen affording dioxetane derivatives [84]. …”

Section: Quasi-intermediate Perepoxidementioning

confidence: 99%

A Mechanistic Spectrum of Chemical Reactions

Inagaki

2009

Orbitals in Chemistry

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The mechanism of chemical reactions between electron donors and acceptors continuously changes with the power of the donors and the acceptors. The interaction between the HOMO (d) of the donors and the LUMO (a*) of the acceptors or delocalization of electrons is important for the reactions. The electron d-to-a* transferred configuration mixes to a significant extent. As the donors and/or the acceptors are strong, their excited configurations appreciably mixes together with the transferred configuration. The d-a and d*-a* orbital interactions are important in addition to the d-a* interaction. Reactions have features characteristic of the excited-state reactions although the donor-acceptor system is not really excited, but in the ground state. This process is termed pseudoexcitation. The a-d-a*-d* interaction is important. For much stronger donors and acceptors, the electron transferred configuration is stable and predominant. Covalent bonds do not form but instead ionic pairs, and electron transfer results. A mechanistic spectrum of chemical reactions is composed of the delocalization, pseudoexcitation, and electron transfer bands.

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Adamantylideneadamantane peroxide, a stable 1,2-dioxetane.

Cited by 124 publications

References 14 publications

Imaging of DNA sequences with chemiluminescence.

Imaging of DNA sequences with chemiluminescence.

Mechanochemical Reactions Reporting and Repairing Bond Scission in Polymers

A Mechanistic Spectrum of Chemical Reactions

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