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Synlett 2016; 27(14): 2145-2149
DOI: 10.1055/s-0035-1561479
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© Georg Thieme Verlag Stuttgart · New York

Controlled Self-Assembly inside C-Shaped Polyaromatic Strips

Mona Sharafi
Department of Chemistry, University of Vermont, Burlington, VT 05405, USA   Email: severin.schneebeli@uvm.edu   Email: jianing.li@uvm.edu
,
Zackariah J. Weinert
Department of Chemistry, University of Vermont, Burlington, VT 05405, USA   Email: severin.schneebeli@uvm.edu   Email: jianing.li@uvm.edu
,
Ian M. Cohen
Department of Chemistry, University of Vermont, Burlington, VT 05405, USA   Email: severin.schneebeli@uvm.edu   Email: jianing.li@uvm.edu
,
Chenyi Liao
Department of Chemistry, University of Vermont, Burlington, VT 05405, USA   Email: severin.schneebeli@uvm.edu   Email: jianing.li@uvm.edu
,
Monika Ivancic
Department of Chemistry, University of Vermont, Burlington, VT 05405, USA   Email: severin.schneebeli@uvm.edu   Email: jianing.li@uvm.edu
,
Jianing Li*
Department of Chemistry, University of Vermont, Burlington, VT 05405, USA   Email: severin.schneebeli@uvm.edu   Email: jianing.li@uvm.edu
,
Severin T. Schneebeli*
Department of Chemistry, University of Vermont, Burlington, VT 05405, USA   Email: severin.schneebeli@uvm.edu   Email: jianing.li@uvm.edu
› Author Affiliations
Further Information

Publication History

Received: 18 April 2016

Accepted: 21 May 2016

Publication Date:
28 June 2016 (online)

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Abstract

Chirality-assisted synthesis (CAS) embodies a powerful strategy for the creation of chiral molecules with well-defined shapes and large cavities. In this communication, we show that C-shaped molecular receptors created with this approach bind to stacks of amphipathic perylenediimide (PDI) dyes. Evidence from 1H NMR titrations, DOSY-NMR studies, and all-atom molecular dynamics simulations indicates that – in the preferred supramolecular binding mode – such polyaromatic strips specifically recognize stacked PDI dimers in solution. These results represent a key step toward the controlled self-assembly of dye molecules inside chiral cavities of shape-persistent, polyaromatic strips.

Key words

supramolecular chemistry - chirality-assisted synthesis - polyaromatic molecular strips - perylene dyes

Supporting Information

    Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0035-1561479.
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  • References and Notes

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