Application of electronic circular dichroism in the study of supramolecular systems.

Chiral supramolecular architectures constitute crucial structural and functional elements in living systems and have been long mimicked by chemists to synthesize new artificial systems endowed with desired properties and functions. Among several techniques to study noncovalent chiral assemblies or aggregates, electronic circular dichroism (ECD) plays a key role because many mechanisms responsible for the appearance of ECD bands occur through space, and therefore are intrinsically sensitive to intermolecular interactions, from short to long-range. The aim of this tutorial review is to emphasize the different kinds of information which can be obtained specifically when chiral supramolecular species are characterized by means of ECD spectroscopy. We will survey several typical applications of ECD in the context of supramolecular chemistry, ranging from the simple detection of chiral aggregates or complexes, to the definition of stoichiometric ratios between the partners, the derivation of thermodynamic and kinetic parameters such as binding and rate constants, and ultimately to the refinement of the most plausible structure of the supramolecular species.

[1]  P. Foggi,et al.  Chirality driven self-assembly in a fluorescent organogel. , 2011, Chirality.

[2]  G. Marconi,et al.  Combination of spectroscopic and computational methods to get an understanding of supramolecular chemistry of drugs: from simple host systems to biomolecules. , 2011, Physical chemistry chemical physics : PCCP.

[3]  P. Thordarson.  Determining association constants from titration experiments in supramolecular chemistry. , 2011, Chemical Society reviews.

[4]  E. W. Meijer,et al.  Insight into the mechanisms of cooperative self-assembly: the "sergeants-and-soldiers" principle of chiral and achiral C3-symmetrical discotic triamides. , 2008, Journal of the American Chemical Society.

[5]  H. Tsukube,et al.  Coordination chemistry strategies for dynamic helicates: time-programmable chirality switching with labile and inert metal helicates. , 2012, Chemical Society reviews.

[6]  R. Naaman,et al.  Electronic and Magnetic Properties of Chiral Molecules and Supramolecular Architectures , 2011 .

[7]  R. Purrello,et al.  Reversible "chiral memory" in ruthenium tris(phenanthroline)-anionic porphyrin complexes. , 2008, Angewandte Chemie.

[8]  N. Berova,et al.  Theoretical analysis of the porphyrin-porphyrin exciton interaction in circular dichroism spectra of dimeric tetraarylporphyrins. , 2003, Journal of the American Chemical Society.

[9]  Z. El-Hachemi,et al.  Hydrodynamic effects on chiral induction. , 2010, Chemical Society reviews.

[10]  E. Yashima,et al.  Thermodynamic and kinetic stabilities of complementary double helices utilizing amidinium-carboxylate salt bridges. , 2012, Journal of the American Chemical Society.

[11]  M. Yamaguchi,et al.  Multiple states of dimeric aggregates formed by (amido-ethynyl)helicene bidomain compound and (amido-ethynyl-amido)helicene tridomain compound. , 2012, Chemistry.

[12]  Stig Allenmark,et al.  Induced circular dichroism by chiral molecular interaction. , 2003, Chirality.

[13]  Z. Bikádi,et al.  Probing the binding of the flavonoid, quercetin to human serum albumin by circular dichroism, electronic absorption spectroscopy and molecular modelling methods. , 2003, Biochemical pharmacology.

[14]  Ana G. Petrovic,et al.  Role of environmental factors on the structure and spectroscopic response of 5'-DNA-porphyrin conjugates caused by changes in the porphyrin-porphyrin interactions. , 2009, Chemistry.

[15]  Ana G. Petrovic,et al.  CD-sensitive Zn-porphyrin tweezer host-guest complexes, part 2: cis- and trans-3-hydroxy-4-aryl/alkyl-beta-lactams. A case study. , 2010, Chirality.

[16]  Christian Wolf,et al.  Chirality sensing using stereodynamic probes with distinct electronic circular dichroism output. , 2013, Chemical Society reviews.

[17]  E. W. Meijer,et al.  Amplification of chirality in dynamic supramolecular aggregates. , 2007, Angewandte Chemie.

[18]  G. Gottarelli,et al.  The use of circular dichroism spectroscopy for studying the chiral molecular self-assembly: an overview. , 2008, Chirality.

[19]  N. Berova,et al.  Conformational aspects in the studies of organic compounds by electronic circular dichroism. , 2011, Chemical Society reviews.

[20]  D. Whitten,et al.  Super-helix formation induced by cyanine J-aggregates onto random-coil carboxymethyl amylose as template. , 2006, Journal of the American Chemical Society.

[21]  Ferenc Zsila,et al.  The drug binding site of human alpha1-acid glycoprotein: insight from induced circular dichroism and electronic absorption spectra. , 2007, Biochimica et biophysica acta.

[22]  L. D. Bari,et al.  Chiroptical Properties of Glucose-Substituted Poly(p-phenylene-ethynylene)s in Solution and Aggregate State , 2012 .

[23]  N. Berova,et al.  Application of electronic circular dichroism in configurational and conformational analysis of organic compounds. , 2007, Chemical Society reviews.

[24]  M. Urbanová,et al.  The location of the high- and low-affinity bilirubin-binding sites on serum albumin: ligand-competition analysis investigated by circular dichroism. , 2013, Biophysical chemistry.

[25]  Jean-Marie Lehn,et al.  Supramolecular chemistry — Scope and perspectives: Molecules — Supermolecules — Molecular devices , 1988 .

[26]  M. Billeter,et al.  Minor-groove binding drugs: where is the second Hoechst 33258 molecule? , 2013, The journal of physical chemistry. B.

[27]  N. Berova,et al.  Comprehensive Chiroptical Spectroscopy , 2011 .

[28]  D. Reinhoudt,et al.  Supramolecular chirality of self-assembled systems in solution. , 2004, Chemical Society reviews.

[29]  E. W. Meijer,et al.  Probing the Solvent-Assisted Nucleation Pathway in Chemical Self-Assembly , 2006, Science.

[30]  S. P. Rath,et al.  Synthesis, structure, and properties of a series of chiral tweezer-diamine complexes consisting of an achiral zinc(II) bisporphyrin host and chiral diamine guest: induction and rationalization of supramolecular chirality. , 2014, Inorganic chemistry.

[31]  Yoshihisa Inoue,et al.  Chirality-sensing supramolecular systems. , 2008, Chemical reviews.

[32]  K. R. Gopidas,et al.  Study of β-Cyclodextrin–Pyromellitic Diimide Complexation. Conformational Analysis of Binary and Ternary Complex Structures by Induced Circular Dichroism and 2D NMR Spectroscopies , 2012 .

[33]  T. Balaban,et al.  Electron Cryo‐Microscopy of TPPS4⋅2HCl Tubes Reveals a Helical Organisation Explaining the Origin of their Chirality† , 2013, Chemphyschem : a European journal of chemical physics and physical chemistry.

[34]  S. Kirschner,et al.  Utilization of the pfeiffer effect and outer-sphere complexation for the prediction of absolute configurations of optically active metal complexes , 1982 .

[35]  S. Neidle.  Quadruplex Nucleic Acids as Novel Therapeutic Targets. , 2016, Journal of medicinal chemistry.

[36]  V. Villari,et al.  Reading of protein surfaces in the native state at micromolar concentrations by a chirogenetic porphyrin probe. , 2012, Chemistry.

[37]  P. Ballester,et al.  Porphyrin tweezer receptors: Binding studies, conformational properties and applications , 2014 .

[38]  W. Marsden.  I and J , 2012 .

[39]  Ana G. Petrovic,et al.  Probing molecular chirality by CD-sensitive dimeric metalloporphyrin hosts. , 2009, Chemical communications.

[40]  R. Purrello,et al.  Vortexes and nanoscale chirality. , 2010, Angewandte Chemie.

[41]  S. Shinkai,et al.  Unexpected chiral induction from achiral cationic polythiophene aggregates and its application to the sugar pattern recognition. , 2012, Chemical communications.

[42]  E. W. Meijer,et al.  Tuning the extent of chiral amplification by temperature in a dynamic supramolecular polymer. , 2010, Journal of the American Chemical Society.