High affinity threading of a new tetralactam macrocycle in water by fluorescent deep-red and near-infrared squaraine dyes

Janel M. Dempsey; Canjia Zhai; Hannah H. McGarraugh; Cynthia L. Schreiber; Shannon E. Stoffel; Andrew Johnson; Bradley D. Smith

doi:10.1039/C9CC05244E

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High affinity threading of a new tetralactam macrocycle in water by fluorescent deep-red and near-infrared squaraine dyes†

Janel M. Dempsey,

^a Canjia Zhai,^a Hannah H. McGarraugh,

^a Cynthia L. Schreiber,^a Shannon E. Stoffel,^a Andrew Johnson^b and Bradley D. Smith

*^a

Author affiliations

* Corresponding authors

^a Department of Chemistry and Biochemistry, University of Notre Dame, 236 Nieuwland Science Hall, Notre Dame, IN 46556, USA
E-mail: smith.115@nd.edu

^b Division of Science, Lindsey Wilson College, 317 Fugitte Science Center, Columbia, KY 42728, USA

Abstract

A new tetralactam macrocycle was prepared and found to encapsulate deep-red and near-infrared squaraine and croconaine dyes in water with tunable threading kinetics. The new supramolecular paradigm of guest back-folding was used to increase macrocycle/squaraine affinity by 370-fold and achieve an association constant of 2.8 × 10⁹ M⁻¹.

This article is part of the themed collection: Cucurbiturils and related cavitands

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Article information

DOI: https://doi.org/10.1039/C9CC05244E
Article type: Communication
Submitted: 08 Jul 2019
Accepted: 20 Sep 2019
First published: 08 Oct 2019

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Chem. Commun., 2019,55, 12793-12796

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High affinity threading of a new tetralactam macrocycle in water by fluorescent deep-red and near-infrared squaraine dyes

J. M. Dempsey, C. Zhai, H. H. McGarraugh, C. L. Schreiber, S. E. Stoffel, A. Johnson and B. D. Smith, Chem. Commun., 2019, 55, 12793 DOI: 10.1039/C9CC05244E

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Chemical Communications

High affinity threading of a new tetralactam macrocycle in water by fluorescent deep-red and near-infrared squaraine dyes†

Abstract

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High affinity threading of a new tetralactam macrocycle in water by fluorescent deep-red and near-infrared squaraine dyes

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