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Molecules 2016, 21(1), 16; doi:10.3390/molecules21010016

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

1
Department of Chemistry-BMC, Uppsala University, Uppsala S-75123, Sweden
2
Department of Chemistry, University of Southampton, Highfield, Southampton SO17 1BJ, UK
*
Author to whom correspondence should be addressed.
Academic Editor: M. Graça P. M. S. Neves
Received: 25 October 2015 / Revised: 21 November 2015 / Accepted: 7 December 2015 / Published: 23 December 2015
View Full-Text   |   Download PDF [6083 KB, uploaded 23 December 2015]   |  

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 Ka = 104–106 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. View Full-Text
Keywords: bisporphyrin tweezers; metalloporphyrins; porphyrinoids; host-guest chemistry; supramolecular chemistry; chirogenesis; chirality transfer; exciton coupled circular dichroism; conformational analysis bisporphyrin tweezers; metalloporphyrins; porphyrinoids; host-guest chemistry; supramolecular chemistry; chirogenesis; chirality transfer; exciton coupled circular dichroism; conformational analysis
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MDPI and ACS Style

Blom, M.; Norrehed, S.; Andersson, C.-H.; Huang, H.; Light, M.E.; Bergquist, J.; Grennberg, H.; Gogoll, A. Synthesis and Properties of Bis-Porphyrin Molecular Tweezers: Effects of Spacer Flexibility on Binding and Supramolecular Chirogenesis. Molecules 2016, 21, 16.

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