14658-94-7Relevant articles and documents
Azulene – Thiophene – Cyanoacrylic acid dyes with donor-π-acceptor structures. Synthesis, characterisation and evaluation in dye-sensitized solar cells
Cowper, Paul,Pockett, Adam,Kociok-K?hn, Gabriele,Cameron, Petra J.,Lewis, Simon E.
, p. 2775 - 2786 (2018)
We report the synthesis of five new azulene containing dyes, having D-π-A type structures. These dyes are synthesised using a sulfonium salt cross-coupling reaction. The dyes have been evaluated spectroscopically, electrochemically, crystallographically, and as sensitizers in dye-sensitized solar cells. We propose a rationale for the dyes’ spectroscopic properties and performance in cells, based on conformational data derived from their crystal structures.
A convenient synthesis of functionalized azulenes via negishi cross-coupling
Dubovik, Julia,Bredihhin, Aleksei
, p. 538 - 548 (2015)
A mild and effective method for the synthesis of functionalized azulenes is described. Negishi cross-coupling of bromoazulenes with functionalized aromatic, heterocyclic, benzylic, and alkylic organozinc reagents affords substituted azulenes in good yields. Functional groups, including ethoxycarbonyl, cyano, methoxy, fluoro, chloro, and bromo are well tolerated. Additionally, a one-pot procedure for introducing two different substituents into positions 1 and 3 of azulene through cross-coupling reaction is described for the first time.
Solution Photochemistry of Azulene
Selco, J. I.,Brooks, T.,Chang, M.,Trieu, M. T.,McDonald, J. K.,McManus, S. P.
, p. 429 - 433 (2007/10/02)
Photochemical reactivity has been observed in solution-phase azulene.Experiments are described which confirm photoinduced deuteration, chlorination, and polymerization.The threshold for the observed chemistry is at the origin of S2 which is at 27956 +/- 8 cm-1 (357.7 +/- 0.1 nm) in chloroform.Only one photon is required to induce the observed chlorine substitution reactions.Although no naphthalene is formed, this chemical channel appears to be the equivalent of a thermal reaction, with the substitutions taking place at the two equivalent positions on the small ring of azulene.The mechanism of these reactions is bimolecular in nature.Chlorination provides a complex mixture of products in most cases; however, deuteration proceeds cleanly giving only 1,3-d2-azulene.
OXIDATIVE SUBSTITUTION XIV. SUBSTITUTION OF HALOGEN IN AROMATIC RING. NEW THEORIES ABOUT THE MECHANISM OF THE ACTION OF CuX2
Nefedov, V.A.,Tarygina, L.K.,Kryuchkova, L.V.,Ryabokobylko, Yu.S.
, p. 487 - 499 (2007/10/02)
The stoichiometry, the comparative reactivity of halogens and hydrogen, the effect of substituents, and the action of an additional oxidizing agent were determined for the reactions of halogenoazulenes with CuX2., leading to substitution of the halogen by the group X (X = Cl, Br, SCN, SeCN, NO2, SO2, Ph).According to model experiments, the equilibrium CuX2 + CuX+ X+ + 2CuX is possible.The reaction of Cu(SO2Ph)2 with Cu(BF4)2 leads to the formation of two equivalents of a copper(I) salt; short-lived particles which substitute the hydrogen and halogen in the substrate are generated during the reaction.It is suggested that the electron generated during oxidation or autooxidation of CuX2 is capable of combining with the substrate.New methods were found for the synthesis of azulene derivatives, and known methods were improved.
BINARY PHASE CHLORINATION OF AROMATIC HYDROCARBONS WITH SOLID COPPER(II) CHLORIDE: REACTION MECHANISM.
Tanimoto,Kushioka,Kitagawa,Maruyama
, p. 3586 - 3591 (2007/10/05)
Anthracene is selectively chlorinated with solid copper(II) chloride to give a quantitative yield of 9-chloroanthracene. The tentative reaction mechanisms so far proposed fail to explain the nonreactivity of some other hydrocarbon homologues, e. g. naphthalene and phenanthrene, toward copper(II) chloride. The present study revealed that the oxidative half-wave potentials (E//1/////2//0//x) of all reactive hydrocarbon homologues were less than 1. 26 V. On the basis of this finding the authors postulate a reaction mechanism involving one electron transfer from hydrocarbon to copper(II) chloride.
