22092-58-6Relevant academic research and scientific papers
Gram-Scale Synthesis and Highly Regioselective Bromination of 1,1,9,9-Tetramethyl[9](2,11)teropyrenophane
Unikela, Kiran Sagar,Roemmele, Tracey L.,Houska, Václav,McGrath, Kaitlin E.,Tobin, David M.,Dawe, Louise N.,Boeré, René T.,Bodwell, Graham J.
, p. 1707 - 1711 (2018)
An improved synthetic pathway to the nanobelt-like 1,1,9,9-tetramethyl[9](2,11)teropyrenophane has been developed, and enables the synthesis of gram quantities of material. Key innovations are the development of a sequential chlorination/Friedel–Crafts alkylation reaction, a sequential iodination/Wurtz coupling reaction, and a room-temperature teropyrene-forming reaction. The teropyrenophane was found to form a very stable radical cation and undergo a completely regioselective fourfold bromination reaction.
1,1,n,n-Tetramethyl[n](2,11)teropyrenophanes (n = 7-9): A series of armchair SWCNT segments
Merner, Bradley L.,Unikela, Kiran Sagar,Dawe, Louise N.,Thompson, David W.,Bodwell, Graham J.
, p. 5930 - 5932 (2013)
A new iterative bridge formation strategy has been employed in the synthesis of a series of [n](2,11)teropyrenophanes (n = 7-9). The generation of the nonplanar teropyrene system, which is calculated to be bent through 178.7°for the smallest homologue (n = 7), is accomplished using a VID reaction of a cyclophanemonoene precursor for the first time.
Gram-Scale Synthesis of the 1,1,n,n-Tetramethyl[n](2,11)teropyrenophanes
Bodwell, Graham J.,Dawe, Louise N.,Ghasemabadi, Parisa Ghods,Houska, Václav,Unikela, Kiran Sagar,Zhao, Yuming
supporting information, p. 390 - 400 (2020/12/03)
A gram-scale synthesis of a series of 1,1,n,n-tetramethyl[n](2,11)teropyrenophanes (n=7–9) has been accomplished as well as the first synthesis of the next higher homologue 1,1,10,10-tetramethyl[10](2,11)teropyrenophane. The scale-up of the original small
The Development of Synthetic Routes to 1,1,n,n-Tetramethyl[n](2,11)teropyrenophanes
Unikela, Kiran Sagar,Merner, Bradley L.,Ghasemabadi, Parisa Ghods,Warford, C. Chad,Qiu, Christopher S.,Dawe, Louise N.,Zhao, Yuming,Bodwell, Graham J.
, p. 4546 - 4560 (2019/07/04)
A concise synthetic approach to 1,1,n,n-tetramethyl[n](2,11)teropyrenophanes has been developed. It involves the construction of triply-bridged pyrenophanes, during which the three bridges are installed successively using Friedel-Crafts alkylation, Wurtz coupling and McMurry reactions. At the same time, the innate regiochemical preferences of pyrene toward electrophilic aromatic substitution are relied upon to control the substitution pattern. A cyclodehydrogenation reaction is then employed to generate the teropyrene system directly in a nonplanar conformation. The crystal structure of 1,1,7,7-tetramethyl[7](2,11)teropyrenophane was determined and the teropyrene system was found to have an end-to-end bend angle of 177.9°.
