A ‘Click Chemistry’ Approach to Graphene-Like Phthalocyanines (Michal Juricek)

Polycyclic aromatic hydrocarbons (PAHs) attract tremendous interest not only because of their excellent optoelectronic properties but also because large PAHs can serve as unique model compounds for super-conductive graphene. However, poor solubility of large PAHs as well as elaborate synthesis complicates processing and application of these structures. We have developed an elegant approach leading to novel functional graphene-like structures via 'click chemistry'. Using triazole moiety as a functional building block we have designed and are constructing unique novel materials with high potential in optoelectronic and magnetic applications and material science. One of the major approaches that are currently under investigation is construction of flat graphene-like phthalocyanine 1 with absorption in the near infrared. We have successfully synthesized 1,2-dibromo-4,5-diiodobenzene, a novel key precursor to octaacetylene phthalocyanine 2, accessible from 1,2-dibromobenzene via iodination method in a cheap quantitative yield. ‘Clicking’ of C₁₂H₂₅N₃ to 2 under standard conditions (CuI/pmdeta) affords 3 in quantitative yield for the first time. .

The goal of this project will be to develop an effective way to connect carbons of the neighboring triazole moieties in 3. This study will first be performed on a simple model system. During this Master project; student will achieve skills in the synthetic organic chemistry including organometallic chemistry and working with exclusion of air and water as well as a range of purification techniques.