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Issue 8, 2018
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Enhanced circular dichroism at elevated temperatures through complexation-induced transformation of a three-layer cyclophane with dualistic dynamic helicity

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Abstract

When two planes stacked one above the other are twisted, they provide a dynamic pair of helical conformations with (M)- or (P)-helicity. We designed a three-layer cyclophane that consists of two such dynamic pairs: the top and middle planes, and the middle and bottom planes. Hence, several global conformations could be created for the overall molecule, e.g., double-helical forms with a pair with the same helicity [(M,M) or (P,P)], and a meso-like form with a pair with a different helicity (M,P). These conformations dynamically interconvert to each other in solution. Chiroptical properties were given by the helical-sense preference of the double-helical forms, which was brought about through complexation with a chiral hydrogen-bonding guest. In terms of the conformational energy in a complexed state, when a desirable relationship between double-helical and meso-like forms was attained, complexation-induced circular dichroism was enhanced at elevated temperatures and decreased at lowered temperatures.

Graphical abstract: Enhanced circular dichroism at elevated temperatures through complexation-induced transformation of a three-layer cyclophane with dualistic dynamic helicity

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Publication details

The article was received on 11 Dec 2017, accepted on 23 Jan 2018 and first published on 23 Jan 2018


Article type: Edge Article
DOI: 10.1039/C7SC05242A
Citation: Chem. Sci., 2018,9, 2222-2229
  • Open access: Creative Commons BY-NC license
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    Enhanced circular dichroism at elevated temperatures through complexation-induced transformation of a three-layer cyclophane with dualistic dynamic helicity

    R. Katoono, Y. Obara, K. Fujiwara and T. Suzuki, Chem. Sci., 2018, 9, 2222
    DOI: 10.1039/C7SC05242A

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