Page 5 of 6
Journal of the American Chemical Society
Supporting Information
1
2
3
4
5
6
7
8
9
The Supporting Information is available free of charge on the
ACS Publications website at DOI: ………
Experimental and theoretical details, 1H NMR spectra of the
complexes, ITC titration data, control experiments, and single-
crystal X-ray data (pdf). Crystallographic data for NC (cif).
Authors.
Yang, T.-L.; Yang, L.-P.; Dang, L.; Jiang, W. Oxatub[5,6]arene:
Synthesis, Conformational Analysis, and the Recognition of C60 and
C70. Chem. Comm. 2017, 53, 336. (d) Jia, F.; Yang, L.-P.; Li, D.-H.;
Jiang, W. Electronic Substituent Effects of Guests on the
Conformational Network and Binding Behavior of Oxatub[4]arene. J.
Org. Chem. 2017, 82, 10444.
(8) (a) Yang, L.-P.; Liu, W.-E.; Jiang, W. Naphthol-Based
Macrocyclic Receptors. Tetrahedron Lett. 2016, 57, 3978. (b) Cui, J.-
S.; Ba, Q.-K.; Ke, H.; Valkonen, A.; Rissanen, K.; Jiang, W.
Directional Shuttling of a Stimuli-Responsive Cone-Like Macrocycle
on a Single-State Symmetric Dumbbell Axle. Angew. Chem. Int. Ed.
2018, 57, 7809. (c) Chai, H.; Yang, L.-P.; Ke, H.; Pang, X.-Y.; Jiang,
W. Allosteric Cooperativity in Ternary Complexes with Low
Symmetry. Chem. Commun. 2018, 54, 7667. (d) Yao, H.; Ke, H.;
Zhang, X.; Pan, S.-J.; Li, M.-S.; Yang, L.-P.; Schreckenbach, G.;
Jiang, W. Molecular Recognition of Hydrophilic Molecules in Water
by Combining the Hydrophobic Effect with Hydrogen Bonding. J.
Am. Chem. Soc. 2018, 140, 13466.
AUTHOR INFORMATION
1
1
1
1
1
1
1
1
1
1
2
2
2
2
2
2
2
2
2
2
3
3
3
3
3
3
3
3
3
3
4
4
4
4
4
4
4
4
4
4
5
5
5
5
5
5
5
5
5
5
6
0
1
2
3
4
5
6
7
8
9
0
1
2
3
4
5
6
7
8
9
0
1
2
3
4
5
6
7
8
9
0
1
2
3
4
5
6
7
8
9
0
1
2
3
4
5
6
7
8
9
0
Notes
The authors declare no competing financial interests.
ACKNOWLEDGMENT
This paper is dedicated to Prof. Julius Rebek Jr. and Prof. Yu Liu
th
th
on the occasion of their 75 and 65 birthdays, respectively. This
research was financially supported by the National Natural
Science Foundation of China (Grant nos. 21572097, 21801125),
the Shenzhen Special Funds (KQJSCX20170728162528382,
JCYJ20170307105848463) and the Shenzhen Nobel Prize Scien-
tists Laboratory Project (C17213101). F. J. thanks the China
Scholarship Council (CSC) for a PhD fellowship. We thank
SUSTech-MCPC for the support with instruments. We thank
Fabian Klautzsch for help with ITC. This work was made possible
using the High-Performance Computing resources of the
Zentraleinrich-tung für Datenverarbeitung (ZEDAT) of Freie
(9) Wang, X.; Hof, F. (How) does 1,3,5-Triethylbenzene
Scaffolding Work? Analyzing the Abilities of 1,3,5-Triethylbenzene-
and 1,3,5-Trimethylbenzene-Based Scaffolds to Preorganize the
Binding Elements of Supramolecular Hosts and to Improve Binding
of Targets. Beilstein J. Org. Chem. 2012, 8, 1.
(10) Turnbull, W. B.; Daranas, A. H. On the Value of c:ꢀ Can Low
Affinity Systems Be Studied by Isothermal Titration Calorimetry? J.
Am. Chem. Soc. 2003, 125, 14859.
Universität
Berlin.
Funding
from
the
Deutsche
(11) Sigurskjold, B. W. Exact Analysis of Competition Ligand
Forschungsgemeinschaft (CRC 765) is gratefully acknowledged.
Binding by Displacement Isothermal Titration Calorimetry. Anal.
Biochem. 2000, 277, 260.
REFERENCES
(12) (a) Müller, A.; Beugholt, C. The Medium is the Message.
Nature, 1996, 383, 296. (b) Beissel, T.; Powers, R. E.; Raymond, K.
N. Symmetry-Based Metal Complex Cluster Formation. Angew.
Chem. Int. Ed. 1996, 35, 1084.
(13) Rebek, J. Jr. Molecular Behavior in Small Spaces. Acc. Chem.
Res. 2009, 42, 1660.
(
1) Cram, D. J. Preorganization—from Solvents to Spherands.
Angew. Chem. Int. Ed. Engl. 1986, 25, 1039.
2) Wittenberg J. B.; Isaacs, L. Complementarity and
(14) Zhai, J.; Xie, X.; Bakker, E. Ionophore-Based Ion-Exchange
Emulsions as Novel Class of Complexometric Titration Reagents.
Chem. Commun. 2014, 50, 12659.
(15) Makarychev-Mikhailov, S.; Shvarev, A.; Bakker, E. Calcium
Pulstrodes with 10-Fold Enhanced Sensitivity for Measurements in
the Physiological Concentration Range. Anal. Chem. 2006, 78, 2744.
(
Preorganization, in Supramolecular Chemistry: From Molecules to
Nanomaterials, John Wiley & Sons, Ltd. 2012.
(3) (a) Zhang. G.; Mastalerz. M. Organic Cage Compounds – from
Shape-Persistency to Function. Chem. Soc. Rev. 2014, 43, 1934; (b)
Hasell, T.; Cooper, A. I. Porous Organic Cages: Soluble, Modular and
Molecular Pores. Nat. Rev. Mater. 2016, 1, 16053; (c) Bisson, A. P.;
Lynch, V. M.; Monahan, M. K. C.; Anslyn, E. V. Recognition of
Anions through NH-π Hydrogen Bonds in a Bicyclic Cyclophane—
Selectivity for Nitrate. Angew. Chem. Int. Ed. 1997, 36, 2340; (d)
Tromans, R. A.; Carter, T. S.; Chabanne, L. Crump, M. P.; Li, H. Y.;
Matlock, J. V.; Orchard, M. M.; Davis, A. P. A Biomimetic Receptor
for Glucose. Nat. Chem. 2019, 11, 52.
(16) Bakker, E.; Buhlmann, P.; Pretsch, E. Carrier-Based Ion-
Selective Electrodes and Bulk Optodes. 1. General Characteristics.
Chem. Rev. 1997, 97, 3083.
(17) For one recent ISEs with micromolar sensitivity: He, C.;
Wang, Z.; Wang, Y.; Hu, R. F.; Li, G. Nonenzymatic All-Solid-State
Coated Wire Electrode for Acetylcholine Determination in vitro.
Biosens. Bioelectron. 2016, 85, 679.
(18) (a) Connelly, N. G.; Geiger, W. E. Chemical Redox Agents
for Organometallic Chemistry. Chem. Rev. 1996, 96, 877. (b) Astruc,
D. Why is Ferrocene So Exceptional? Eur. J. Inorg. Chem. 2017, 1,
(4) Sanders, J. K. M. Supramolecular Catalysis in Transition.
Chem. Eur. J. 1998, 4, 1378.
6
. (c) Ochi, Y.; Suzuki, M.; Imaoka, T.; Murata, M.; Nishihara, H.;
(5) Borgia, A.; Borgia, M. B.; Bugge, K.; Kissling, V. M.;
Heidarsson, P. O.; Fernandes, C. B.; Sottini, A.; Soranno, A.;
Buholzer, K. J.; Nettels, D.; Kragelund, B. B.; Best, R. B.; Schuler, B.
Extreme Disorder in an Ultrahigh-Affinity Protein Complex. Nature
Einaga, Y.; Yamamoto, K. Controlled Storage of Ferrocene
Derivatives as Redox-Active Molecules in Dendrimers. J. Am. Chem.
Soc. 2010, 132, 5061. (d) White, N. G.; Beer, P. D. A Ferrocene
Redox-Active Triazolium Macrocycle That Binds and Senses
Chloride. Beilstein J. Org. Chem. 2012, 8, 246.
2
018, 555, 61.
6) Houk, K. N.; Leach, A. G.; Kim, S. P.; Zhang, X. Binding
(
(19) (a) Nakahata, M.; Takashima, Y.; Yamaguchi, H.; Harada, A.
Affinities of Host-Guest, Protein-Ligand, and Protein-Transition-State
Complexes. Angew. Chem. Int. Ed. 2003, 42, 4872.
Redox-Responsive Self-Healing Materials Formed from Host–Guest
Polymers. Nat. Commun. 2011, 2, 511. (b) Ahn, Y.; Jang, Y.;
Selvapalam, N.; Yun, G.; Kim, K. Supramolecular Velcro for
Reversible Underwater Adhesion. Angew. Chem., Int. Ed. 2013, 52,
(7) (a) Jia, F.; He, Z.; Yang, L.-P.; Pan, Z.-S.; Yi, M.; Jiang, R.-W.;
Jiang, W. Oxatub[4]arene: a Smart Macrocyclic Receptor with
Multiple Interconvertible Cavities. Chem. Sci. 2015, 6, 6731. (b) Jia,
F.; Wang, H.-Y.; Li, D.-H. ; Yang, L.-P.; Jiang, W. Oxatub[4]arene: a
Molecular “Transformer” Capable of Hosting a Wide Range of
Organic Cations. Chem. Comm. 2016, 52, 5666. (c) Jia, F.; Li, D.-H.;
3
140. (c) Ni, M.; Zhang, N.; Xia, W.; Wu, X.; Yao, C.; Liu, X.; Hu,
X.-Y.; Lin, C.; Wang, L. Dramatically Promoted Swelling of a
Hydrogel by Pillar[6]arene–Ferrocene Complexation with
Multistimuli Responsiveness. J. Am. Chem. Soc. 2016, 138, 6643.
Table of Contents (TOC) Graphic
ACS Paragon Plus Environment
5