Synthesis of bicyclo[5.3.0]azulene derivatives

The following protocol is the general procedure used for synthesizing methyl 2-methylazulene-1-carboxylate. It is optimized for reactions up to the 10-mmol scale. Detailed reaction conditions, setups and purification of the products by column chromatography are described. Although the reactions use anhydrous solvents in the presence of a static argon atmosphere, the starting materials are not particularly sensitive to air; therefore, no intensive care is required.

Pfau-Plattner azulene synthesis | Analytical Wiki | …

Synthesis and Crystal Structure of A Novel Cadmium Complex with Sodium Azulene Sulfonate[J].

Synthesis of azulene from 6-acyloxyfulvenes - …

We report the synthesis of novel azulene-substituted methacrylate polymers by free radical polymerization, in which the azulene moieties represent hydrophobic dipoles strung pendant to the polymer backbone and impart unique electronic properties to the polymers. Tunable optoelectronic properties were realized by adjusting the azulene density, ranging from homopolymers (having one azulene group per repeat unit) to copolymers in which the azulene density was diluted with other pendant groups. Treating these polymers with organic acids revealed optical and excitonic behavior that depended critically on the azulene density along the polymer chain. Copolymers of azulene with zwitterionic methacrylates proved useful as cathode modification layers in bulk-heterojunction solar cells, where the relative azulene content affected the device metrics and the power conversion efficiency reached 7.9%.

A new azulene synthesis - Journal of the Chemical …

Synthetic routes to azulene have long been of interest becauseof its unusual structure. An efficient route entails of with unsaturated C5-. Thealternative approach from has long been known,one illustrative method being shown below.

Pfau-Plattner Azulene Synthesis - Chempedia - …

Azulene has been recognized for its application in medicinal therapy against inflammation. Recently, azulene analogs have been used in optical technology. Nevertheless, synthesis of this family of compounds is always associated with multiple challenges. In this protocol, we describe a time-efficient and cost-effective procedure for the preparation of azulene derivatives from 2-hydroxycyclohepta-2,4,6-trienone (tropolone), a readily available starting material. The technique illustrated here involves a cycloaddition reaction of a lactone with the in situ-generated vinyl ether from 2,2-dimethoxypropane during the thermolysis reaction. The three-step synthesis should take


The Aromaticity of Azulene
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Azulene vs Napthalene
Why is naphthalene more stable than azulene?

Synthesis of An Azulene Ring System by Singlet Oxygen …

Azulene derivatives have many useful applications. It has a brilliant blue color, and the tuning of its optical properties has led to many azulenic chromophores. Some of the most notable and useful derivatives of azulene are those that absorb in the near-infrared region (NIR) of the electromagnetic spectrum. NIR-absorbing compounds are useful imaging agents as they allow for imaging of deeper tissue because they absorb light in the ‘NIR window,’ a region of the spectrum (650–900 nm) where hemoglobin and water have their lowest absorption coefficients. Azulene derivatives have also found use as building blocks for potent pharmaceuticals. Modifications of the five- and seven-membered rings have led to the development of compounds that were found to have antioxidant, antiallergenic, antiarrhythmic, anticancer and local anesthetic activities. Non-benzenoid bicyclic azulenes are also important intermediates in the synthesis of various useful compounds for mechanistic studies of cyclic conjugations and high-technology applications. The utility of azulene derivatives is largely because of their inimitable structure of a bicyclic hydrocarbon containing asymmetric pi electrons, which result in a cyclopenta-dienyl anion and a tropylium cation. Although such a separation of charges occurs only to a slight extent, it has a very marked effect on the physical and chemical properties of azulene. For instance, the cyclopentadiene of azulene is very reactive toward electrophilic substitution reactions. The aromaticity of this five-membered ring of azulene has been the subject of several important modifications, namely Friedel–Crafts acylations, Mannich aminomethylations, condensations and Vilsmeier formylations,,, among others. On the other hand, the tropylium cation is suitable for use in nucleophilic reactions and is a subject of interest representing a class of nonbenzenoid aromatic compounds,.