Synthesis and Characterization of Poly(2,6-triptycene)

Abstract

We report the syntheses of two monomers, 2,6-dibromotriptycene and 2,6-diiodotriptycene, and their applications in the homopolymerization via a nickel(0)-mediated Yamamoto-type polycondensation polymerization, leading to a novel aromatic polymerspoly(2,6-triptycene). This new polymer was characterized by 1 H and 13 C NMR spectroscopy, which exhibited an excellent match with the NMR spectra of the model compound, 2,2′-bitriptycene. In addition, the polymer was found to be highly soluble in common organic solvents, although it does not contain any flexible side chains. This good solubility was attributed to its high content of triptycene units, whose rigid three-dimensional structure was proposed to prevent dense packing of polymer chains. A highly transparent film could be obtained by spin-casting a chloroform solution. This polymer also demonstrated good thermal stability.

High Performance Polyimide with High Internal Free Volume Elements

“…Recently, poly(2,6-triptycene) was synthesized via a nickel-mediated Yamamoto-type polycondensation polymerization. [21] This polymer was highly soluble in common organic solvents despite a lack of swivel groups, because of its high rigid triptycene content and lack of dense polymer packing. In addition, more recently, the soluble polyimides were prepared by the formation of intrinsic microporosity via the incorporation of 908-kinked spiro-centers into the polymer backbone, [22] or the formation of a hypercrosslinked network.…”

Photochromic dithienylethene-branched triptycene hybrids

“…Starting material 7a, 7b and borate ester 9 were prepared according to modified literature procedures [23,24]. Intermediate 11 and 12 were prepared according to the methods reported by Swager [25] and Chen [26], respectively. Target compound 1 and intermediate 8, 10 were prepared according to our previous work [21].…”

Synthesis of Substituted Iptycenes

“…At present, the isolation of dinitrotriptycenes can only be accomplished by separation through solvent treatment or column chromatography of a mixture of nitration products. 33 Recently, Mastalerz and coworkers 34 reported that treatment of triptycene (1) with fuming nitric acid and heating at 80-85 °C for four hours gave the further nitration product, 2,3,6,7,13,14-hexanitrotriptycene (62) in a yield of 18% (Scheme 18).…”