Camphorquinone, also known as 2,3-bornanedione, is an

organic compound Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-co ...

derived from

camphor Camphor () is a waxy, colorless solid with a strong aroma. It is classified as a terpenoid and a cyclic ketone. It is found in the wood of the camphor laurel (''Cinnamomum camphora''), a large evergreen tree found in East Asia; and in the kapu ...

. A yellow solid, it is used as a

photoinitiator In chemistry, a photoinitiator is a molecule that creates reactive species (free radicals, cations or anions) when exposed to radiation (Ultraviolet, UV or Visible spectrum, visible). Synthetic photoinitiators are key components in photopolymers ...

in curing

dental composite Dental composite resins (better referred to as "resin-based composites" or simply "filled resins") are dental cements made of synthetic resins. Synthetic resins evolved as restorative materials since they were insoluble, of good tooth-like appea ...

s. Camphorquinone is produced by the oxidation of

with

selenium dioxide Selenium dioxide is the chemical compound with the formula SeO2. This colorless solid is one of the most frequently encountered compounds of selenium. It is used in making specialized glasses as well as a reagent in organic chemistry. Properties ...

Photocuring details

Polymerization is induced very slowly by camphorquinone, so amines such as N,N-dimethyl-p-toluidine, 2-ethyl-dimethylbenzoate, N-phenylglycine are generally added to increase the rate of curing. It absorbs very weakly at 468 nm ( extinction coefficient of 40 M⁻¹·cm⁻¹) giving it a pale yellow color. Photoexcitation results in nearly quantitative formation of its triplet state through

intersystem crossing Intersystem crossing (ISC) is an isoenergetic radiationless process involving a transition between the two electronic states with different spin multiplicity. Excited singlet and triplet states When an electron in a molecule with a singlet grou ...

and very faint fluorescence.

Reactions

It can be hydrolyzed by the enzyme 6-oxocamphor hydrolase. Camphorquinone has been examined as a reagent in

organic synthesis Organic synthesis is a branch of chemical synthesis concerned with the construction of organic compounds. Organic compounds are molecules consisting of combinations of covalently-linked hydrogen, carbon, oxygen, and nitrogen atoms. Within the gen ...

References

{{Reflist Ketones Monoterpenes