Chiral Iodotriptycenes: Synthesis and Catalytic Applications

Abstract

Invited for this month′s cover picture is the group of Thomas Wirth at Cardiff University (UK). The cover picture shows two structures of triptycenes. In each of these molecules all three aromatic rings are different with the rigid structure of the molecules making them chiral. The two sp3‐carbons shown in red and green are the stereocentres with defined configuration. These molecules contain the crucial iodine functionality which are utilised to generate hypervalent iodine(III)‐catalysts in situ. The authors acknowledge Dr. Yu Wang for the creation of the cover image. Read the full text of their Research Article at 10.1002/open.202200145.

Tuning Porosity in Triptycene-Poly(arylene ether)s

“…Scheme 2a shows the chiral separation of (R,R)-tBu-TRP-OH, which is inspired by the separation of chiral iodotriptycenes. 29 First, (1S)-(−)-camphanic chloride (R*-Cl) was installed through an esterification reaction with rac-tBu-TRP-OH to produce a mixture of tBu-TRP-OR* diastereomers. The tBu-TRP-OR* diastereomers were readily separated via recrystallization in dichloromethane, eliminating the need for chromatographic purification.…”

“…4,4′-Dibromobiphenyl is an unactivated aryl bromide and unsuitable for S N Ar reactions, so we followed the previously reported Pd-catalyzed polycondensation to polymerize rac - t Bu-TRP-OH and 4,4′-dibromobiphenyl and yielded M n = 15.6 kDa rac -PAE-H (Scheme b). Scheme a shows the chiral separation of ( R , R )- t Bu-TRP-OH, which is inspired by the separation of chiral iodotriptycenes . First, (1 S )-(−)-camphanic chloride (R*-Cl) was installed through an esterification reaction with rac - t Bu-TRP-OH to produce a mixture of t Bu-TRP-OR* diastereomers.…”