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      Synthesis and Properties of Bis-Porphyrin Molecular Tweezers: Effects of Spacer Flexibility on Binding and Supramolecular Chirogenesis

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          Abstract

          Ditopic binding of various dinitrogen compounds to three bisporphyrin molecular tweezers with spacers of varying conformational rigidity, incorporating the planar enediyne ( 1), the helical stiff stilbene ( 2), or the semi-rigid glycoluril motif fused to the porphyrins ( 3), are compared. Binding constants K a = 10 4–10 6 M −1 reveal subtle differences between these tweezers, that are discussed in terms of porphyrin dislocation modes. Exciton coupled circular dichroism (ECCD) of complexes with chiral dinitrogen guests provides experimental evidence for the conformational properties of the tweezers. The results are further supported and rationalized by conformational analysis.

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          Determining association constants from titration experiments in supramolecular chemistry.

          Pall Thordarson (2011)
          The most common approach for quantifying interactions in supramolecular chemistry is a titration of the guest to solution of the host, noting the changes in some physical property through NMR, UV-Vis, fluorescence or other techniques. Despite the apparent simplicity of this approach, there are several issues that need to be carefully addressed to ensure that the final results are reliable. This includes the use of non-linear rather than linear regression methods, careful choice of stoichiometric binding model, the choice of method (e.g., NMR vs. UV-Vis) and concentration of host, the application of advanced data analysis methods such as global analysis and finally the estimation of uncertainties and confidence intervals for the results obtained. This tutorial review will give a systematic overview of all these issues-highlighting some of the key messages herein with simulated data analysis examples.
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            Application of electronic circular dichroism in configurational and conformational analysis of organic compounds.

            Nina Berova, Lorenzo Di Bari, Gennaro Pescitelli (2007)
            This tutorial review is addressed to readers with a background in basic organic chemistry and spectroscopy, but without a specific knowledge of electronic circular dichroism. It describes the fundamental principles, instrumentation, data analysis, and different approaches for interpretation of ECD. The discussion focuses on the application of ECD, also in combination with other methods, in structural analysis of organic compounds, including host-guest complexes, and will emphasize the importance of the interplay between configurational and conformational factors. The tutorial also covers modern supramolecular aspects of ECD and recent developments in computational methods.
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              Macromodel?an integrated software system for modeling organic and bioorganic molecules using molecular mechanics

              Fariborz Mohamadi, Nigel G. J. Richards, Wayne Guida … (1990)
              Article 0 comments Cited 209 times – based on 0 reviews     Review now
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                Author and article information

                Contributors
                M. Graça P. M. S. Neves: Role: Academic Editor
                Journal
                Journal ID (nlm-ta): Molecules
                Journal ID (iso-abbrev): Molecules
                Journal ID (publisher-id): molecules
                Title: Molecules
                Publisher: MDPI
                ISSN (Electronic): 1420-3049
                Publication date (Electronic): 23 December 2015
                Publication date Collection: January 2016
                Volume: 21
                Issue: 1
                Electronic Location Identifier: 16
                Affiliations
                [1 ]Department of Chemistry-BMC, Uppsala University, Uppsala S-75123, Sweden; magnus.blom@ 123456kemi.uu.se (M.B.); sara.norrehed@ 123456raa.se (S.N.); claes.henrik.andersson@ 123456gmail.com (C.-H.A.); hao.huang@ 123456angstrom.uu.se (H.H.); jonas.bergquist@ 123456kemi.uu.se (J.B.); helena.grennberg@ 123456kemi.uu.se (H.G.)
                [2 ]Department of Chemistry, University of Southampton, Highfield, Southampton SO17 1BJ, UK; light@ 123456soton.ac.uk
                Author notes
                [* ]Correspondence: adolf.gogoll@ 123456kemi.uu.se ; Tel.: +46-184-713-822
                Article
                Publisher ID: molecules-21-00016
                DOI: 10.3390/molecules21010016
                PMC ID: 6274253
                PubMed ID: 26703562
                SO-VID: d7237074-0165-4f00-b7af-e73acb0ce939
                Copyright © © 2015 by the authors.
                License:

                Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons by Attribution (CC-BY) license ( http://creativecommons.org/licenses/by/4.0/).

                History
                Date received : 25 October 2015
                Date accepted : 07 December 2015
                Categories
                Subject: Article

                Keywords: bisporphyrin tweezers,metalloporphyrins,porphyrinoids,host-guest chemistry,supramolecular chemistry,chirogenesis,chirality transfer,exciton coupled circular dichroism,conformational analysis
                Data availability:
                Keywords: bisporphyrin tweezers, metalloporphyrins, porphyrinoids, host-guest chemistry, supramolecular chemistry, chirogenesis, chirality transfer, exciton coupled circular dichroism, conformational analysis

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