Biobased Poly(Schiff-Base) Composed of Bifurfural

Abstract

In this study, bifurfural, an inedible biobased chemical and a second-generation biomass, was polymerized with several diamines using an environmentally benign process, and the chemical structures of the resulting poly(Schiff base)s were analyzed. Because furan rings, which are only produced from biomass and not from fossil resources, endow polymers with unique properties that include high rigidity and expanded π-conjugation, bifurfural, which contains two furan rings, is of significant interest as a biobased building block. 1 H NMR, IR, and matrix assisted laser desorption ionization-time of flight mass spectra of the poly(Schiff base)s reveal that they are composed of mixtures of linear and cyclic structures. The UV–vis spectroscopy and molecular orbital theory confirm the extended π-conjugation in the bifurfural/ p -phenylenediamine poly(Schiff base) system. Poly(Schiff base)s composed of bifurfural and 1,3-propanediamine, 1,4-butandiamine, 1,5-pentanediamine, and 1,6-hexanediamine were molded at 120 °C into films that exhibited good strengths and were tough to bend. These results indicate that bifurfural-based poly(Schiff base)s are promising biobased materials.

Dual-Modular Aptasensor for Detection of Cardiac Troponin I Based on Mesoporous Silica Films by Electrochemiluminescence/Electrochemical Impedance Spectroscopy

“…Here, one new characteristic peak at 1635 cm −1 demonstrates the formation of the imine bond (−CN−, a Schiff base), in line with that reported in the literature. 48 In a word, all of these results evidenced that the amino-functional aptamer is successfully coupled on the sensing substrate.…”

“…Furthermore, the disappearance of the peak at 286 nm means the consumption of mono-GA. Also the FT-IR spectra of GA, amino-Apt, and GA-Apt (Figure D) presented more information of the connection. Here, one new characteristic peak at 1635 cm –1 demonstrates the formation of the imine bond (−CN–, a Schiff base), in line with that reported in the literature . In a word, all of these results evidenced that the amino-functional aptamer is successfully coupled on the sensing substrate.…”

Furan Polymers: State of the Art and Perspectives

“…The latest addition to this family of furan polymers reports the synthesis and characterization of poly(Schiff base)s from 2,2‐bifuryl,5,5‐dialdehyde and different diamines, whose general linear structure is shown in Figure , but cyclic oligomers were also formed in these systems. [ 44 ]…”

Upgrading the chemistry of π-conjugated polymers toward more sustainable materials

“…118 This experimental protocol was published in 2000 and surprisingly no development could be found afterwards. Nowadays, reports on difurfural synthesis actually describe a longer experimental protocol, with a protection/deprotection step but also the use of palladium-based catalyst, 119,120 as shown in Scheme 17. Furan-based compounds are promising building blocks and could be comparable to thiophene and may even be better than the latter, thanks to their efficient πstacking and strong fluorescence.…”

“…Polymer 13 has an absorbance maximum at 442 nm -the authors did not optically characterize further these polyazomethines, as they were interested in their mechanical properties. 119…”