Biomass-derived rctt-3,4-di-2-furanyl-1,2-cyclobutanedicarboxylic acid: a polytopic ligand for synthesizing green metal-organic materials

A biorenewable cyclobutane-containing building block synthesized from sorbic acid using photoenergy

“…Last but not least, a one-dimensional (1D) linear network of hydrogen bonds (O C=O ···O OH = 2.62 − 2.67 Å, Figure 5 C and ESI) in the crystal of CBDA-3 shows its potential in preparing supramolecular materials like hydrogen-bonded organic frameworks (HOFs) ( Hou et al., 2014b ; Wang et al., 2014 ) and green metal-organic materials (GMOMs). ( Chu et al., 2018 ; Shahni et al., 2021 ; Stock and Biswas, 2012 )

Figure 5 The X-ray single crystal structure of CBDA-3 (A and B) Two views of the crystal structure in Oak Ridge Thermal Ellipsoid Plot (ORTEP) representing 50% electron density (except for hydrogen atoms). The cyclobutane ring is highlighted in blue with the 18.5° torsion angle apparent in the second image.

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“…(Coates and Hillmyer, 2009;Kovash et al, 2014;Lligadas et al, 2013;Rajendran et al, 2015;Tschan et al, 2012;Wang et al, 2015aWang et al, , 2015b To work toward a solution to this problem, our research group has recently been synthesizing a series of cyclobutane-containing diacid building blocks (CBDAs) made from biomass-derived starting materials (Figure 1). (Amjaour et al, 2019;Reagen et al, 2021;Shahni et al, 2020Shahni et al, , 2021Wang et al, 2017Wang et al, , 2018Wang et al, , 2020Wang et al, , 2022 Recent examples include CBDA-1 and CBDA-4, (Amjaour et al, 2019;Shahni et al, 2020;Wang et al, 2017Wang et al, , 2022 both derived from cinnamic acid, and CBDA-2, (Reagen et al, 2021;Shahni et al, 2021;Wang et al, 2018Wang et al, , 2020 derived from 2-furanacrylic acid. Both of these starting acids can be readily obtained from various biomass sources such as DDGS (Dried Distillers Grains with Sulubles), corn cobs, wheat bran, sawdust, or sugarcane bagasse.…”

Diverse Applications of Biomass‐Derived 5‐Hydroxymethylfurfural and Derivatives as Renewable Starting Materials

“…[85] The CBDA-2 ligand has also been utilized as a ligand for the synthesis of green metal-organic materials (GMOM), demon-strated through the synthesis of two 2D coordination polymers with Cu and Co that exhibit thermochromic behaviors. [88]…”

“…The washed and collected MOFs exhibited gas adsorption capabilities for N 2 , H 2 , and CO 2 and magnetic properties. Since then, other MOFs with FDCA linkers have been made with Gd, [91] as well as with Cu, [88,89] Cr, [92] Fe, [89,93] Zr, [89,92,93] Zn, [94] various lanthanides, [90,91,95] and, most commonly, Al. [89,93,[96][97][98][99][100][101][102][103][104][105][106][107] The polarity and conjugation of the FDCA ligands confers desirable properties in MOFs designed for metal binding and detection through photoluminescence.…”

“…The washed and collected MOFs exhibited gas adsorption capabilities for N 2 , H 2 , and CO 2 and magnetic properties. Since then, other MOFs with FDCA linkers have been made with Gd, [91] as well as with Cu, [88,89] Cr, [92] Fe, [89,93] Zr, [89,92,93] Zn, [94] various lanthanides, [90,91,95] and, most commonly, Al [89,93,96–107] …”