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Title: Supramolecular Double-Helix Formation by Diastereoisomeric Conformations of Configurationally Enantiomeric Macrocycles

Abstract

Solid-state superstructures, resulting from assemblies programmed by homochirality, are attracting considerable attention. In addition, artificial double-helical architectures are being investigated, especially in relation to the ways in which homochiral small molecules can be induced to yield helical forms as a result of chiral induction. In this work, we report the highly specific self-assembly upon crystallization of a double-helical superstructure from an enantiopure macrocyclic dimer which adopts two diastereoisomeric conformations in a molar ratio of 1.5:1 in dimethyl sulfoxide. These two conformational diastereoisomers self-organize—and self-sort—in the crystalline phase in equimolar proportions to form two single-handed helices which are complementary to each other, giving rise to the assembly of a double helix that is stabilized by intermolecular [C–H···O] and π–π stacking interactions. The observed self-sorting phenomenon occurs on going from a mixed-solvent system containing two equilibrating conformational diastereoisomers, presumably present in unequal molar proportions, into the solid state. The diastereoisomeric conformations are captured upon crystallization in a 1:1 molar ratio in the double-helical superstructure, whose handedness is dictated by the choice of the enantiomeric macrocyclic dimer. The interconversion of the two conformational diastereoisomers derived from each configurationally enantiomeric macrocycle was investigated in CD3SOCD3 solution by variable-temperature 1H NMR spectroscopy (VT NMR) andmore » circular dichroism (VT CD). The merging of the resonances for the protons corresponding to the two diastereoisomers at a range of coalescence temperatures in the VT NMR spectra and occurrence of the isosbestic points in the VT CD spectra indicate that the two diastereoisomers are interconverting slowly in solution on the 1H NMR time scale but rapidly on the laboratory time scale. To the best of our knowledge, the self-assembly of such solid-state superstructures from two conformational diastereoisomers of a homochiral macrocycle is a rare, if not unique, occurrence.« less

Authors:
 [1];  [1];  [1];  [1];  [1];  [1]
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  1. Northwestern Univ., Evanston, IL (United States)
Publication Date:
Research Org.:
Energy Frontier Research Centers (EFRC) (United States). Center for Bio-Inspired Energy Science (CBES); Northwestern Univ., Evanston, IL (United States)
Sponsoring Org.:
USDOE Office of Science (SC), Basic Energy Sciences (BES)
OSTI Identifier:
1388750
Grant/Contract Number:  
SC0000989
Resource Type:
Accepted Manuscript
Journal Name:
Journal of the American Chemical Society
Additional Journal Information:
Journal Volume: 138; Journal Issue: 43; Related Information: CBES partners with Northwestern University (lead); Harvard University; New York University; Pennsylvania State University; University of Michigan; University of Pittsburgh; Journal ID: ISSN 0002-7863
Publisher:
American Chemical Society (ACS)
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; catalysis (homogeneous); solar (photovoltaic); bio-inspired; charge transport; mesostructured materials; materials and chemistry by design; synthesis (novel materials); synthesis (self-assembly); superstructures; aromatic compounds; conformation; nuclear magnetic resonance spectroscopy; macrocycles

Citation Formats

Samanta, Avik, Liu, Zhichang, Nalluri, Siva Krishna Mohan, Zhang, Yu, Schatz, George C., and Stoddart, J. Fraser. Supramolecular Double-Helix Formation by Diastereoisomeric Conformations of Configurationally Enantiomeric Macrocycles. United States: N. p., 2016. Web. doi:10.1021/jacs.6b09258.
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Samanta, Avik, Liu, Zhichang, Nalluri, Siva Krishna Mohan, Zhang, Yu, Schatz, George C., & Stoddart, J. Fraser. Supramolecular Double-Helix Formation by Diastereoisomeric Conformations of Configurationally Enantiomeric Macrocycles. United States. https://doi.org/10.1021/jacs.6b09258
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Samanta, Avik, Liu, Zhichang, Nalluri, Siva Krishna Mohan, Zhang, Yu, Schatz, George C., and Stoddart, J. Fraser. Thu . "Supramolecular Double-Helix Formation by Diastereoisomeric Conformations of Configurationally Enantiomeric Macrocycles". United States. https://doi.org/10.1021/jacs.6b09258. https://www.osti.gov/servlets/purl/1388750.
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@article{osti_1388750,
title = {Supramolecular Double-Helix Formation by Diastereoisomeric Conformations of Configurationally Enantiomeric Macrocycles},
author = {Samanta, Avik and Liu, Zhichang and Nalluri, Siva Krishna Mohan and Zhang, Yu and Schatz, George C. and Stoddart, J. Fraser},
abstractNote = {Solid-state superstructures, resulting from assemblies programmed by homochirality, are attracting considerable attention. In addition, artificial double-helical architectures are being investigated, especially in relation to the ways in which homochiral small molecules can be induced to yield helical forms as a result of chiral induction. In this work, we report the highly specific self-assembly upon crystallization of a double-helical superstructure from an enantiopure macrocyclic dimer which adopts two diastereoisomeric conformations in a molar ratio of 1.5:1 in dimethyl sulfoxide. These two conformational diastereoisomers self-organize—and self-sort—in the crystalline phase in equimolar proportions to form two single-handed helices which are complementary to each other, giving rise to the assembly of a double helix that is stabilized by intermolecular [C–H···O] and π–π stacking interactions. The observed self-sorting phenomenon occurs on going from a mixed-solvent system containing two equilibrating conformational diastereoisomers, presumably present in unequal molar proportions, into the solid state. The diastereoisomeric conformations are captured upon crystallization in a 1:1 molar ratio in the double-helical superstructure, whose handedness is dictated by the choice of the enantiomeric macrocyclic dimer. The interconversion of the two conformational diastereoisomers derived from each configurationally enantiomeric macrocycle was investigated in CD3SOCD3 solution by variable-temperature 1H NMR spectroscopy (VT NMR) and circular dichroism (VT CD). The merging of the resonances for the protons corresponding to the two diastereoisomers at a range of coalescence temperatures in the VT NMR spectra and occurrence of the isosbestic points in the VT CD spectra indicate that the two diastereoisomers are interconverting slowly in solution on the 1H NMR time scale but rapidly on the laboratory time scale. To the best of our knowledge, the self-assembly of such solid-state superstructures from two conformational diastereoisomers of a homochiral macrocycle is a rare, if not unique, occurrence.},
doi = {10.1021/jacs.6b09258},
journal = {Journal of the American Chemical Society},
number = 43,
volume = 138,
place = {United States},
year = {Thu Oct 06 00:00:00 EDT 2016},
month = {Thu Oct 06 00:00:00 EDT 2016}
}
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https://doi.org/10.1021/jacs.6b09258
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Figures / Tables:

Figure 1 Figure 1: Synthesis of R-2BTDI and R-2BPDI along with a schematic representation of the self-assembly upon crystallization of a complementary supramolecular double helix which turns out to be an equimolar mixture of two conformational diastereoisomers of R-2BTDI.
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