2018
DOI: 10.1021/acs.cgd.8b01044
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Abstract: A set of three positional isomeric nitro-phenyl functionalized linear bis-urea scaffolds has been purposefully synthesized from p-phenylenediamine, basically for investigating the extensive anion-coordination behavior in their neutral form. The para-isomer (L 1 ) and meta-isomer (L 2 ) can readily form bicarbonate dimer (HCO3)2 entrapped neutral self-assemblies in the solid state by either fluoride or hydroxide induced atmospheric CO2 fixation. In the bulk scale and based on the isolated yield of (HCO3)2 ent… Show more

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Cited by 9 publications
(5 citation statements)
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References 68 publications
(75 reference statements)
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“…At the higher concentrations used for cyclic voltammetric and preparative scale electrolysis experiments (i.e., 1 mM), k obs is inversely correlated with the concentration of Fe- para -urea , presumably due to a dimerization process occurring in solution (Figure S2). Similar dimers generated through H-bond templating with exogenous anions have been extensively observed for linear bis-urea ligands, which may explain the lower-than-expected observed activity of Fe- para -urea .…”
Section: Resultssupporting
confidence: 72%
See 1 more Smart Citation
“…At the higher concentrations used for cyclic voltammetric and preparative scale electrolysis experiments (i.e., 1 mM), k obs is inversely correlated with the concentration of Fe- para -urea , presumably due to a dimerization process occurring in solution (Figure S2). Similar dimers generated through H-bond templating with exogenous anions have been extensively observed for linear bis-urea ligands, which may explain the lower-than-expected observed activity of Fe- para -urea .…”
Section: Resultssupporting
confidence: 72%
“…To illustrate the general concept for this current study, we chose iron tetraphenylporphyrin ( Fe-TPP ) as a representative member of a prototypical class of molecular CO 2 RR catalysts. Inspired by the field of anion receptor chemistry, , we sought to enhance the interaction of the Fe-TPP catalyst with bicarbonate by incorporating a bis-aryl urea moiety into the second coordination sphere (Figure ). (Thio)­ureas are known to be highly effective motifs for selective binding of bicarbonate and other oxyanions and thus have been incorporated into diverse frameworks, such as amide-linked macrocycles, cyclopeptide cages, and tripodal and linear ligand scaffolds for recognition and sensing applications. Indeed, previous reports from our laboratory ,, and others have established the ability of second coordination sphere pendants to enhance CO 2 RR catalysis.…”
Section: Resultsmentioning
confidence: 99%
“…At the higher concentrations used for cyclic voltammetric and preparative scale electrolysis experiments (i.e., 1 mM), kobs is inversely correlated with the concentration of Fe-para-urea, presumably due to a dimerization process occurring in solution (Figures S2). Similar dimers generated through H-bond templating with exogenous anions have been extensively observed for linear bisurea ligands, 27 which may explain the lower-than-expected observed activity of Fe-para-urea.…”
Section: Resultssupporting
confidence: 65%
“…[17][18][19][20][21] Inspired by the field of anion receptor chemistry, 22,23 we sought to enhance the interaction of the Fe-TPP catalyst with bicarbonate by incorporating a bis-aryl urea moiety into the second coordination sphere (Figure 1). (Thio)ureas are known to be highly effective motifs for selective binding of bicarbonate and other oxyanions, and thus have been incorporated into diverse frameworks such as amide-linked macrocycles, 24 cyclopeptide cages, 25 and tripodal 26 and linear [27][28][29][30][31] ligand scaffolds for recognition and sensing applications. Indeed, previous reports from our laboratory 6,32,33 and others [34][35][36][37][38][39][40][41][42][43][44][45][46][47] have established the ability of second coordination sphere pendants to enhance CO2RR catalysis.…”
Section: Resultsmentioning
confidence: 99%
“…Compounds PNBA (p-nitrobenzoyl azide) and PMBA (p-methoxybenzoyl azide) were prepared using previously published procedures. 1 Compound DU (1,1'-(1,4-phenylene)bis(3-(4-nitrophenyl)urea)) 2 and MA (N-(4-aminophenyl)-4-nitrobenzamide) 3 were previously prepared and characterized, and analyses of herein prepared MA and DU products were compared to published results.…”
mentioning
confidence: 99%