Boron Nitride-Doped Polyphenylenic Organogels

Abstract

Herein, we describe the synthesis of the first boron nitride-doped polyphenylenic material obtained through a [4 + 2] cycloaddition reaction between a triethynyl borazine unit and a biscyclopentadienone derivative, which undergoes organogel formation in chlorinated solvents (the critical jellification concentration is 4% w/w in CHCl 3 ). The polymer has been characterized extensively by Fourier-transform infrared spectroscopy, solid-state 13 C NMR, solid-state 11 B NMR, and by comparison with the isolated monomeric unit. Furthermore, the polymer gels formed in chlorinated solvents have been thoroughly characterized and studied, showing rheological properties comparable to those of polyacrylamide gels with a low crosslinker percentage. Given the thermal and chemical stability, the material was studied as a potential support for solid-state electrolytes. showing properties comparable to those of polyethylene glycol-based electrolytes, thus presenting great potential for the application of this new class of material in lithium-ion batteries.

Synthesis and Applications of Organic Borazine Materials

“…2019 [ 127] B,N-AC 2017 [27] (Continued) 2019 [ 132] P(AB-3HT-) CV: 2019 [ 104] (Continued) 2022 [ 133] BLP-1(H) (P14a) or Cu (111) surfaces. On Au (111), a hexagonal pattern is visible in the STM images (Figure 12), where each molecule has three neighbors in a propeller-like arrangement.This structure appears to be both porous and chiral, allowing for clockwise or anti-clockwise arrangements.…”

“…Very recently, Dosso, Bonifazi and coworkers [ 133 ] succeeded to realize the first borazino‐bearing polyphenylenic gel material ( P13 , Figure 5) by a polymerization exploiting the [4 + 2] cycloaddition reaction between a B‐triethynyl borazine unit and a biscyclopentadienone derivative. The BN doped polymer was obtained in 52% yield, and efficiently formed organogels in chlorinated solvents, with a 4 wt.% critical jellification concentration when CHCl 3 was used.…”

Accessing Borazine Substitution Patterns through Late‐Stage Iodination

“…Organic borazines have gained substantial attention due to their unique properties and potential applications in various fields including (opto)electronics, [1–6] catalysis, [7,8] and the broader domain of materials science [9–13] . Hexa‐aryl borazines, in particular, have been demonstrated to be valuable precursors to doped‐nanographenes, [2,14] and doped‐polyphenylenes [15,16] . More in general, the borazine ring serves as a stable doping unit in materials displaying unique electronic and optical properties [1,5,14,17] .…”

“…[9][10][11][12][13] Hexa-aryl borazines, in particular, have been demonstrated to be valuable precursors to dopednanographenes, [2,14] and doped-polyphenylenes. [15,16] More in general, the borazine ring serves as a stable doping unit in materials displaying unique electronic and optical properties. [1,5,14,17] However, the potential of these intriguing compounds has been somewhat constrained due to harsh conditions generally utilized for their synthesis that are also accompanied by several side reactions due to the inherent instability of aryl borazine precursors.…”

A waste-minimized approach for the synthesis of iodinated organic borazines

“…For example, borazines have been used for the construction of dendrimeric polyphenylenes, 15 or for assembling doped organogels. 16…”