ArticleJournal of the American Chemical Society2007
Self-assembly of fluorescent inclusion complexes in competitive media including the interior of living cells.
Article in Journal of the American Chemical Society, 2007. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 28 papers.
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Who cites it
28 citing papers in PubMed.
- A Metallosupramolecular Receptor for Squaraine Dyes Enabling Ultrafast Dark Resonance Energy Transfer.Angewandte Chemie (International ed. in English) · 2026Article
- A Synthetic Lectin for Glucuronate.ACS central science · 2025Article
- Mechanical insulation of aza-Pechmann dyes within [2]rotaxanes.Chemical science · 2024Article
- Charge transport modulation in pseudorotaxane 1D stacks of acene and azaacene derivatives.Chemical science · 2019Article
- Molecular recognition using tetralactam macrocycles with parallel aromatic sidewalls.Beilstein journal of organic chemistry · 2019Review
- New tetralactam hosts for squaraine dyes.Organic & biomolecular chemistry · 2018Article
- Fluorescent Thienothiophene-Containing Squaraine Dyes and Threaded Supramolecular Complexes with Tunable Wavelengths between 600⁻800 nm.Molecules (Basel, Switzerland) · 2018Article
- Crystal structure and solvent-dependent behaviours of 3-amino-1,6-diethyl-2,5,7-trimethyl-4,4-di-phenyl-3a,4a-di-aza-4-bora-Acta crystallographica. Section E, Crystallographic communications · 2017Article
- Complex lasso: new entangled motifs in proteins.Scientific reports · 2016Article
- Pre-Assembly of Near-Infrared Fluorescent Multivalent Molecular Probes for Biological Imaging.Bioconjugate chemistry · 2016Article
- High Affinity Macrocycle Threading by a Near-Infrared Croconaine Dye with Flanking Polymer Chains.The journal of physical chemistry. B · 2016Article
- Sensitive Structural Control of Macrocycle Threading by a Fluorescent Squaraine Dye Flanked by Polymer Chains.Organic letters · 2015Article
- Rapid Macrocycle Threading by a Fluorescent Dye-Polymer Conjugate in Water with Nanomolar Affinity.Journal of the American Chemical Society · 2015Article
- In vivo imaging of bone using a deep-red fluorescent molecular probe bearing multiple iminodiacetate groups.Molecular pharmaceutics · 2013Article
- Bovine serum albumin nanoparticles with fluorogenic near-IR-emitting squaraine dyes.ACS applied materials & interfaces · 2013Article
- Convenient Synthesis of Multivalent Zinc(II)-Dipicolylamine Complexes for Molecular Recognition.Tetrahedron letters · 2013Article
- A comparative study of semi-squaraine and squaraine dyes using computational techniques: tuning the charge transfer/biradicaloid character by substitution.Journal of molecular modeling · 2013Article
- A simple and accessible synthetic lectin for glucose recognition and sensing.Nature chemistry · 2012Article
- A double-stranded DNA rotaxane.Nature nanotechnology · 2010Article
- Microwave-assisted slipping synthesis of fluorescent squaraine rotaxane probe for bacterial imaging.Chemical communications (Cambridge, England) · 2010Article
Corrections and comments
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Authors and funding
8 authors.
Funding
Abstract
Anthracene-containing tetralactam macrocycles are prepared and found to have an extremely high affinity for squaraine dyes in chloroform (log Ka = 5.2). Simply mixing the two components produces highly fluorescent, near-infrared inclusion complexes in quantitative yield. An X-ray crystal structure shows the expected hydrogen bonding between the squaraine oxygens and the macrocycle amide NH residues, and a high degree of cofacial aromatic stacking. The kinetics and thermodynamics of the assembly process are very sensitive to small structural changes in the binding partners. For example, a macrocycle containing two isophthalamide units associates with the squaraine dye in chloroform 400,000 times faster than an analogous macrocycle containing two 2,6-dicarboxamidopyridine units. Squaraine encapsulation also occurs in highly competitive media such as mixed aqueous/organic solutions, vesicle membranes, and the organelles within living cells. The highly fluorescent inclusion complexes possess emergent properties; that is, as compared to the building blocks, the complexes have improved chemical stabilities, red-shifted absorption/emission maxima, and different cell localization propensities. These are useful properties for new classes of near-infrared fluorescent imaging probes.
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