title: Method for the preparation of derivatives of heptiptycene: toward dual-cavity baskets.
abstract: We have developed a novel synthetic method that enables the preparation of functional derivatives of heptiptycene, i.e., cavitands with two juxtaposed cavities. The homocoupling of bicyclic dibromoalkenes is promoted by Pd(OAc)2 (10%) in dioxane (100 °C) to give cyclotrimers in 27-77% yield under optimized reaction conditions (Ph3P, K2CO3, n-Bu4NBr, N2, 4 Å MS). These dual-cavity baskets show a strong π → π* absorption at 241 nm (ε = 939,000 M(-1) cm(-1)), along with a subsequent fluorescence emission at 305 nm.
authors: Department of Chemistry and Biochemistry, The Ohio State University, 100 West 18th Avenue, Columbus, Ohio 43210, USA.
authors: Keith
authors: K
authors: Hermann
authors: Stephen
authors: S
authors: Sardini
authors: Yian
authors: Y
authors: Ruan
authors: Ryan J
authors: RJ
authors: Yoder
authors: Mrinal
authors: M
authors: Chakraborty
authors: Shubham
authors: S
authors: Vyas
authors: Christopher M
authors: CM
authors: Hadad
authors: Jovica D
authors: JD
authors: Badjić
mesh_terms: D000873:Anthracenes / Q000138:chemical synthesis* / Q000737:chemistry; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000737:chemistry*; D006842:Hydrocarbons, Brominated / Q000737:chemistry*; D008958:Models, Molecular; D008968:Molecular Conformation
chemical_list: D000873:Anthracenes; D019086:Bridged Bicyclo Compounds, Heterocyclic; D006842:Hydrocarbons, Brominated; C583507:heptiptycene