Abstract
The rational design of wholly synthetic receptors that bind active substrates with ultrahigh affinities is a challenging goal, especially in water. Here, we report the synthesis of a tricyclic octacationic cyclophane, which exhibits complementary stereoelectronic binding toward a widely used fluorescent dye, perylene diimide, with picomolar affinity in water. The ultrahigh binding affinity is sustained by a large and rigid hydrophobic binding surface, which provides a highly favorable enthalpy and a slightly positive entropy of complexation. The receptor-substrate complex shows significant improvement in optical properties, including red-shifted absorption and emission, turn-on fluorescence, and efficient energy transfer. An unusual single-excitation, dual-emission, imaging study of living cells was performed by taking advantage of a large pseudo-Stokes shift, produced by the efficient energy transfer.
Original language | English (US) |
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Pages (from-to) | 3165-3173 |
Number of pages | 9 |
Journal | Journal of the American Chemical Society |
Volume | 142 |
Issue number | 6 |
DOIs | |
State | Published - Feb 12 2020 |
Funding
The authors thank Professor Bradley D. Smith and Professor Douglas Philp for their insightful comments and suggestions on the manuscript. The authors also thank Dr. Margaret Schott for helping to polish the language in the manuscript. This research is part of the Joint Center of Excellence in Integrated Nano-Systems (JCIN) at King Abdulaziz City for Science and Technology (KACST) and Northwestern University (NU). The authors would like to thank both KACST and NU for their continued support of this research. The cell imaging research performed at the Biological Imaging Facility at Northwestern University is graciously supported by the Chemistry of Life Processes Institute, the NU Office for Research, and the Rice Foundation.
ASJC Scopus subject areas
- Catalysis
- General Chemistry
- Biochemistry
- Colloid and Surface Chemistry
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CCDC 1952502: Experimental Crystal Structure Determination
Liu, W. (Contributor), Bobbala, S. (Contributor), Stern, C. L. (Contributor), Hornick, J. E. (Contributor), Liu, Y. (Contributor), Enciso, A. E. (Contributor), Scott, E. A. (Contributor) & Fraser, S. J. (Contributor), Cambridge Crystallographic Data Centre, 2020
DOI: 10.5517/ccdc.csd.cc23jqyb, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc23jqyb&sid=DataCite
Dataset
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CCDC 1952501: Experimental Crystal Structure Determination
Liu, W. (Contributor), Bobbala, S. (Contributor), Stern, C. L. (Contributor), Hornick, J. E. (Contributor), Liu, Y. (Contributor), Enciso, A. E. (Contributor), Scott, E. A. (Contributor) & Fraser, S. J. (Contributor), Cambridge Crystallographic Data Centre, 2020
DOI: 10.5517/ccdc.csd.cc23jqx9, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc23jqx9&sid=DataCite
Dataset
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CCDC 1952500: Experimental Crystal Structure Determination
Liu, W. (Contributor), Bobbala, S. (Contributor), Stern, C. L. (Contributor), Hornick, J. E. (Contributor), Liu, Y. (Contributor), Enciso, A. E. (Contributor), Scott, E. A. (Contributor) & Fraser, S. J. (Contributor), Cambridge Crystallographic Data Centre, 2020
DOI: 10.5517/ccdc.csd.cc23jqw8, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc23jqw8&sid=DataCite
Dataset