Homochiral coordination polymers with nanotubular channels for enantioselective sorption of chiral guest molecules

Abstract

† Electronic supplementary information (ESI) available: Synthesis of (R)-PCP-4a and 4b, general procedure for guest sorption experiment and X-ray diffraction study. CCDC 954513 and 954514. For ESI and crystallographic data in CIF or other electronic format see

Progress in the synthetic and functional aspects of chiral metal–organic frameworks

“…The structural isomer of L 18 , 1,3-bis-IJimidazol-1ylmethyl) benzene (L 19 ), has been reported earlier by Mukherjee et al, exhibiting spontaneous resolution and leading to the fabrication of a 1D CP conglomerate, ij(L 20 )ZnCl 2 ] (28). 81 Another interesting MOF, {[AgIJL 21 )]IJBF 4 )•0.5tetrahydrofuran} n , (29) produced by spontaneous resolution has been reported by Manzano and coworkers. 82a The reaction of bisIJ3,5-dimethylpyrazol-1-yl)IJpyridine-4-yl)methane (L 21 ) with AgBF 4 and subsequent crystallization in a combination of solvents (methylene chloride, tetrahydrofuran and acetone) resulted in conglomerate 29.…”

“…6 In particular, the synthesis of homochiral MOFs has been a frontier research topic in recent years due to their potential applications in the fields of asymmetric catalysis, enantioselective separation, magnetism, non-linear optics and chiral recognition. [7][8][9][10][11][12][13][14][15][16][17][18][19][20][21][22][23][24] Homochiral MOFs are usually synthesized by direct and reliable methodologies, whereby metal precursors are treated with enantiopure organic ligands. Homochiral MOFs comprising chiral linkers have already been proven good candidates towards applications in asymmetric catalysis.…”

Emerging enantiomeric resolution materials with homochiral nano-fabrications

“…[107][108][109] Some of the binaphthyl and biphenol derivatives have also been introduced as bridging ligands for chiral MOFs preparation and applied in the field of chiral selective adsoption and fluorescent recognition. [84][85][86] In early studies, Lin and co-workers have employed a 1,1′-bi-2-naphthol (BINOL) derivative to assemble metal-organic supramolecule with well defined chiral pockets, [Cl(CO) 3 Re(BINOL 1 )] 4 (BINOL 1 = 6,6′-dichloro-2,2′-dihydroxyl-1,1′-binaphthyl-4,4′-bipyridine), that exhibited enantio-selective luminescence quenching by chiral amino alcohols. 82 To improve the enantio-selectivity, they developed a type of highly porous and fluorescent MOFs that built from BINOL derivatives and cadmium recently.…”

“…[107][108][109] Some of the binaphthyl and biphenol derivatives also have been introduced as bridging ligands for chiral MOFs preparation and applied in the field of chiral selective adsorption and fluorescence recognition. [84][85][86] In early studies, Lin and co-workers employed a 1,1′-bi-2-naphthol (BINOL) derivative to assemble a metal-organic supramolecule with well-defined chiral pockets, [Cl(CO) 3 Re-(BINOL 1 )] 4…”

Chirality control of self-assembled achiral nanofibers using amines in their solid state

“…6 In a recent example, coordination polymers have demonstrated their potential use as receptors for enantioselective recognition. 7 In the solution state, supramolecular systems formed from achiral molecules have also shown the ability to induce or otherwise change their self-assembly to generate helical supramolecular systems offering a means for chiral recognition. Many such systems have employed ammonium-carboxylate salt bridging to facili-tate control of the helical supramolecular assemblies, [8][9][10][11] though a number of other interesting transformation schemes have also been devised in the solution state including several studies demonstrating the control of helical polymeric systems by the Yashima group.…”