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N-Centered Chiral Self-Sorting and Supramolecular Helix of Troger's Base-Based Dimeric Macrocycles in Crystalline State.

ABSTRACT: Three stereoisomers of Tröger's Base-based dimeric macrocycles Trögerophane 1 (T1) including one pair of enantiomers ( rac-T1) and one meso isomer ( R 2N S 2N -T1) were obtained and fully characterized by X-ray analysis. In the crystalline stacking state R 2N S 2N -T1 showed heterochiral self-sorting behavior along a axis with cofacial ?-? stacking interactions, while rac-T1 showed heterochiral self-sorting behavior along c axis with slipped ?-? stacking interactions, respectively. Meanwhile both of them showed homochiral self-sorting behavior along b axis as well as one pair of supramolecular helixes were formed in both cases. All the self-sorting behaviors are controlled by two chiral Tröger's Base units from neighboring molecules. To the best of our knowledge, such chiral self-sorting and supramolecular helixes of N-centered chiral superstructures is a rare example. In addition, R 2N S 2N -T1 and rac-T1 demonstrated different adsorption capacities toward the vapor of dichloromethane and acetone, respectively.

SUBMITTER: Chen Y

PROVIDER: S-EPMC6555195 | biostudies-literature | 2019

REPOSITORIES: biostudies-literature

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N-Centered Chiral Self-Sorting and Supramolecular Helix of Tröger's Base-Based Dimeric Macrocycles in Crystalline State.

Chen Yuan Y Cheng Ming M Hong Benkun B Zhao Qian Q Qian Cheng C Jiang Juli J Li Shuhua S Lin Chen C Wang Leyong L

Frontiers in chemistry 20190531

Three stereoisomers of Tröger's Base-based dimeric macrocycles Trögerophane 1 (T1) including one pair of enantiomers ( rac-T1) and one meso isomer ( R 2N S 2N -T1) were obtained and fully characterized by X-ray analysis. In the crystalline stacking state R 2N S 2N -T1 showed heterochiral self-sorting behavior along a axis ...[more]

PMID: 31214566

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Project description:A V-Shaped 4-amino-1,8-napthalimide derived tetracarboxylic acid linker (L; bis-[N-(1,3-benzenedicarboxylic acid)]-9,18-methano-1,8-naphthalimide-[b,f][1,5]diazocine) comprising the Tröger's base (TB) structural motif was rationally designed and synthesised to access a nitrogen-rich fluorescent supramolecular coordination polymer. By adopting the straight forward precipitation method, a new luminescent nanoscale Zn(ii) coordination polymer (TB-Zn-CP) was synthesized in quantitative yield using Zn(OAc)2·2H2O and tetraacid linker L (1?:?0.5) in DMF at room temperature. The phase-purity of as-synthesised TB-Zn-CP was confirmed by X-ray powder diffraction analysis, infra-red spectroscopy, and elemental analysis. Thermogravimetric analysis suggests that TB-Zn-CP is thermally stable up to 330 °C and the morphological features of TB-Zn-CP was analysed by SEM and AFM techniques. The N2 adsorption isotherm of thermally activated TB-Zn-CP at 77 K revealed a type-II reversible adsorption isotherm and the calculated Brunauer-Emmett-Teller (BET) surface area was found to be 72 m2 g-1. Furthermore, TB-Zn-CP displayed an excellent CO2 uptake capacity of 76 mg g-1 at 273 K and good adsorption selectivity for CO2 over N2 and H2. The aqueous suspension of as-synthesized TB-Zn-CP showed strong green fluorescence (?max = 520 nm) characteristics due to the internal-charge transfer (ICT) transition and was used as a fluorescent sensor for the discriminative sensing of nitroaromatic explosives. The aqueous suspension of TB-Zn-CP showed the largest quenching responses with high selectivity for phenolic-nitroaromatics (4-NP, 2,4-DNP and PA) even in the concurrent presence of other potentially competing nitroaromatic analytes. The fluorescence titration studies also provide evidence that TB-Zn-CP detects picric acid as low as the parts per billion (26.3 ppb) range. Furthermore, the observed fluorescence quenching responses of TB-Zn-CP towards picric acid were highly reversible. The highly selective fluorescence quenching responses including the reversible detection efficiency make the nanoscale coordination polymer TB-Zn-CP a potential material for the discriminative fluorescent sensing of nitroaromatic explosives.

Dataset Information

N-Centered Chiral Self-Sorting and Supramolecular Helix of Troger's Base-Based Dimeric Macrocycles in Crystalline State.

Publications

<i>N</i>-Centered Chiral Self-Sorting and Supramolecular Helix of Tröger's Base-Based Dimeric Macrocycles in Crystalline State.

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