Iodide ion receptors: shape-persistent macrocycles ofsyn/anticonfigurations

Article abstract of DOI:10.1039/d1nj00247c

This article reports a pair of rigid iodide ion macrocyclic receptors ofsyn/anticonfigurations. Single crystal X-ray analysis confirms the structure of thesyn-isomers, and¹H Nuclear Magnetic Resonance (¹H NMR) titration and ultraviolet-visible (UV-Vis) absorption are used to study the binding affinity of the isomers to halogen ions. Both the isomers show colorimetric and fluorescence recognition towards iodide anions in dichloromethane solution. By solving the association constants, it can be concluded that the interaction between theanti-isomer and iodide ions is relatively weaker than that in thesyn-isomer, and thesyn-isomer has much better recognition selectivity for I^?in CH₂Cl₂than theanti-isomer. The results of the theoretical calculations show thatsyn/anticonfigurations bring about different orientations of the alkyl chains, leading to the larger steric hindrance of theanti-isomer to hinder the combination with iodide ions, and thesynconfigurations with relatively smaller steric hindrance can enhance the binding between the isomers and the iodide anions. A shape persistent macrocycle with a bound conformation can be looked at as a special case of conformational selection, and the results of this study indicate a local induced fit mechanism following a conformational selection in the recognition of iodide anions, and we anticipate that this work will help to understand these two dominant binding mechanisms in molecular recognition and have a certain reference value for designing better anion receptors.

Full text of DOI:10.1039/d1nj00247c

NJC
View Article Online
View Journal | View Issue
PAPER
Iodide ion receptors: shape-persistent
macrocycles of syn/anti configurations†
Cite this: New J. Chem., 2021,
45, 6796
Guang-Wei Zhang,a Jia-Yin Xiang,a Tao-Tao Zhong,a Xin-Ru Zhi,a Chuang Gao,a
a
abc
Wei Huang,
Shuai Yuan,a Ling-Hai Xiea and Wei Huang
*
This article reports a pair of rigid iodide ion macrocyclic receptors of syn/anti configurations. Single crystal X-ray
1
analysis confirms the structure of the syn-isomers, and H Nuclear Magnetic Resonance (1H NMR) titration and
ultraviolet-visible (UV-Vis) absorption are used to study the binding affinity of the isomers to halogen ions. Both
the isomers show colorimetric and fluorescence recognition towards iodide anions in dichloromethane solution.
By solving the association constants, it can be concluded that the interaction between the anti-isomer and
iodide ions is relatively weaker than that in the syn-isomer, and the syn-isomer has much better recognition
selectivity for IÀ in CH2Cl2 than the anti-isomer. The results of the theoretical calculations show that syn/anti
configurations bring about different orientations of the alkyl chains, leading to the larger steric hindrance of the
anti-isomer to hinder the combination with iodide ions, and the syn configurations with relatively smaller steric
hindrance can enhance the binding between the isomers and the iodide anions. A shape persistent macrocycle
with a bound conformation can be looked at as a special case of conformational selection, and the results of
this study indicate a local induced fit mechanism following a conformational selection in the recognition of
iodide anions, and we anticipate that this work will help to understand these two dominant binding mechanisms
in molecular recognition and have a certain reference value for designing better anion receptors.
Received 15th January 2021,
Accepted 5th March 2021
DOI: 10.1039/d1nj00247c
rsc.li/njc
extensively explored, such as the pre-organization of the recep-
tors and the complementary three-dimensional electronic
Introduction
Anions play an indispensable role in various fields.1–6 For arrangement.13 Among them, the research of macrocyclic
example, phosphate is an important product of the metabolic compounds plays an important leading role. Macrocycles with
process of organisms, and the hydrogen sulfate ion is an pre-organized binding sites have strong binding affinity to
important component of acid rain.7–9 Therefore, it is of great specific objects.14–17 Generally speaking, the shape persistence
significance to study the application of anion recognition in the of macrocyclic receptors18,19 for anions can increase the pre-
fields of chemistry, life materials science, environmental organization to enhance binding affinities due to the well-
science, etc.10 In the past few decades, many anion receptors defined conformational space, and when the cavity of a
have been widely reported,11,12 and the main factors affecting shape-persistent macrocycle offers a poor match to the guest,
the interaction between receptors and anions have been binding is reduced. Such receptors would have high selectivity
biased toward guests with complementary size and shape. The
narrow conformational freedom of the shape-persistent macro-
cycle also allows supramolecular interactions encoded in the
a Centre for Molecular Systems and Organic Devices (CMSOD), Key Laboratory for
Organic Electronics and Information Displays and Jiangsu Key Laboratory for
molecular framework to be maintained under various condi-
tions, and provides greater opportunities for successful molecular
design.
Biosensors, Institute of Advanced Materials (IAM), Nanjing University of Posts and
Telecommunications, 9 Wenyuan Road, Nanjing, 210023, China
b Frontiers Science Center for Flexible Electronics (FSCFE), MIIT Key Laboratory of
Flexible Electronics (KLoFE), Shaanxi Key Laboratory of Flexible Electronics,
Xi’an Key Laboratory of Flexible Electronics, Xi’an Key Laboratory of Biomedical
Materials & Engineering, Xi’an Institute of Flexible Electronics,
Institute of Flexible Electronics (IFE), Northwestern Polytechnical University,
Xi’an 710072, Shaanxi, China
As further impetus for our work, many macrocycle-based
anion receptors toward halide ions have been reported. There
are some good examples such as [4]chrysaorene reported by
Stepien and coworkers that binds halide ions with a particular
selectivity toward iodides,16 Huang’s cyclo[4]carbazole that
combines iodide anions,17 tetrazines reported by Wang and
coworkers that form diverse complexes with anions of different
geometries and shapes20 and that form complexes with
chlorides,21 bambusurils reported by Heck that show good
c Key Laboratory of Flexible Electronics (KloFE) & Institute of Advanced Materials
(IAM), Nanjing Tech University (NanjingTech), 30 South Puzhu Road,
Nanjing 211816, China. E-mail: iamwhuang@nwpu.edu.cn
† Electronic supplementary information (ESI) available. CCDC 1911554. For
crystallographic data in CIF or other electronic format. See DOI: 10.1039/
d1nj00247c
This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2021
6796
| New J. Chem., 2021, 45, 6796–6802

View Article Online
Paper
NJC
affinity toward iodide anions22 and by Sindelar that bind iodide than 1 nm to a few nanometres, with clear angles and vertices
anions,23 sulfonamides24 and tetraamido isophthaloyl macrocycles25 in the nanometre range, and may become good anion accep-
reported by Georghiou that form
a complex with tetra-n- tors, which would have high selectivity biased toward guests
butylammonium halides, cyclodextrins reported by Roy that form with complementary size and shape.34 The NH group has been
inclusion complexation of tetrabutylammonium iodide,26 and calix- proved to be an effective site for anion recognition.35–37 The
pyrroles reported by Namor that perform as hosts for halide disparity in electronegativity (0.84)38 between nitrogen and
anions.27 In short, only a few of the macrocycles synthesized in hydrogen leads to bond polarization and the capability of
the above literature studies are rigid.16,17
hydrogen-bond donation. NH groups are prevalent in several
In general, a shape-dynamic host would be more appro- organic functional moieties such as amines, amides, and ureas
priate to target guests with a broader class of shapes, and a and in heterocycles like pyrrole. The synthetic modularity
shape persistent host would have high selectivity biased toward surrounding NH groups has led to their incorporation into an
guests with complementary size and shape, as shape persis- abundance of well-studied receptors, of which only a few are
tence serves to increase the preorganization of the host to rigid macrocycles,39–42 therefore we introduced the NH group
enhance binding affinity. Cram defined the concept of into the rigid macrocyclic skeleton and synthesized a pair of
preorganization28 as follows: ‘‘the more highly hosts and guests rigid macrocyclic syn/anti isomers. As far as we know, the
are organized for binding and low solvation prior to their influence of isomers in anion recognition by rigid macrocycles
complexation, the more stable will be their complexes.’’ The has rarely been reported before,43–46 so the present research
shape persistency brings minimal conformational heterogene- work was carried out to study the recognition towards halogen
ity, and thus many benefits have evolved such as easy and anions of these two isomers in dichloromethane. Both the
predictable molecular design and more straightforward under- isomers have pre-existing bound conformations and halogen
standing of recognition behaviors. Recently the mechanism anions select one of them for binding, which is similar to
governing the interactions of macrocycles with its molecular conformational selection, and thus the study of the interaction
target has regained people’s attention.29 The explanation of between the anions and the isomers could help to understand
molecular recognition has evolved from the simple host–guest the binding mechanisms in molecular recognition.
association to the understanding of the key role played by
conformational changes. A shape persistent macrocycle has a
bound conformation, which can be looked at as a special case
of conformational selection to a certain extent, and related
Results and discussion
studies could enable understanding of two dominant binding Based on the Friedel–Crafts reaction, syn-isomer, anti-isomer
mechanisms such as induced fit and conformational selection and th-isomer were synthesized from L-carbazole tertiary alcohol 8
in molecular recognition.
under the catalysis of BF3ÁEt2O (Scheme 1). The synthons 8 can be
In previous work, we have successfully synthesized a series prepared in three ways. The first way is to use 3-bromocarbazole 1
of luminescent rigid macrocyclic compounds via the Friedel– and tertiary alcohol borate pinacolato ester 7 to obtain synthon 8
Crafts reactions.30–33 These macrocycles have non-collapsible through the Suzuki reaction. The second way is to generate
backbones and inside cavities, ranging in size from slightly less synthons by the Suzuki coupling reaction of carbazole boronic
Scheme 1 The synthetic routes of syn/anti isomers. The green arrow indicates the first method of preparing the L-carbazole tertiary alcohol synthon,
the red one indicates the second, and the blue one indicates the third.
This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2021
New J. Chem., 2021, 45, 6796–6802
| 6797

View Article Online
NJC
Paper
acid pinacol ester 4 with 2-bromo tertiary alcohol 5. The third
way is to obtain carbazole fluorenone 6 through the reaction of
carbazole boronic acid pinacol ester 4 and 2-bromo-9-fluorenone
2, and then obtain synthon 8 through Grignard reaction. It is
easier to separate and purify by the second approach and the yield
is the highest at 55% (Fig. S1–S9, ESI†).
The receptors syn-isomer and anti-isomer were synthesized
following the steps described in Scheme 1 and characterized by
standard spectroscopy techniques 1H NMR (Fig. S11, ESI†) and
single crystal X-ray diffraction analysis. The ability of the
receptors to recognize certain anions in the solution was
evaluated by 1H NMR spectroscopy using CD2Cl2 as the solvent.
In the absence of anions, the characteristic peaks of syn-isomer
and anti-isomer are at 7.98, 8.24 ppm and 8.29, 8.00 ppm,
corresponding to the N–H of carbazole and the K position
proton of fluorene, respectively (Fig. 1).
Fortunately, the single crystal of syn-isomer was obtained by
slowly evaporating from the 2 : 5 chloroform/isopropanol mixed
solution, and its structure was confirmed by single crystal X-ray
analysis (Fig. 2), while the single crystal of anti-isomer was not
been obtained. In the front view (Fig. 2a), all nitrogen atoms are
located outside the cavity and face the same direction, forming
a concave boat conformation. The average distance between
two nuclei of hydrogen (Ha and Hb) is 9.40 Å, and the van der
Waals radius of the hydrogen atom is 1.20 Å,47 which means
that the diameter of the NH–NH of syn-isomer is about 7.00 Å.
This diameter between N–H groups of the receptors is larger
than that of halide ions, such as iodide ion (4.40 Å),47 and is a
suitable distance for hydrogen bond formation. The crystal
structure shows that the cavity formed between the NH groups
of syn-isomer is pre-organized, and its size is suitable for
binding of iodide ions (Fig. 2b). In order to evaluate this,
commercially available tetrabutylammonium salts (TBAX,
X = FÀ, ClÀ, BrÀ, IÀ) were added to the receptors dissolved in
dichloromethane (TBAX has good solubility in dichloro-
methane), and the interactions between the receptors and
halogen anions were studied.
Fig. 2 (a) Ellipse view of the X-ray crystal structure of syn-isomer. (b) The
simulated complex between syn-isomer and iodide ion. Nitrogen atoms
are blue, oxygen atoms are red, and hydrogen atoms are omitted for
clarity.
Fig. 3 shows part of the 1H NMR spectra of the two receptors
after binding to TBAI (tetrabutylammonium iodide). All
1H NMR titrations were performed at a concentration of 5
mM. Upon addition of 4.87 equivalents of TBAI, the N–H peak
of carbazole shifts to the low field by +1.07 ppm of syn-isomer
(Fig. 3i). When the concentration increases to 13.48 equiva-
lents, the N–H signal peak of carbazole continues to move to
the low field with a displacement of +0.93 ppm. This phenom-
enon may be due to the formation of a non-covalent bond
between the encapsulated electron withdrawing IÀ and the
Fig. 1 (a) Partial 1H NMR spectra of syn-isomer in CD2Cl2 at 25 1C. (b) Partial 1H NMR spectra of anti-isomer in CD2Cl2 at 25 1C.
This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2021
6798
| New J. Chem., 2021, 45, 6796–6802

View Article Online
Paper
NJC
inferred that syn/anti configurations bring about different
orientations of the alkyl chains according to the results of the
theoretical calculations (Fig. S12, ESI†), so the steric hindrance
of the anti-isomer hinders the combination with iodide ions,
and thus the interactions between the NH protons in the anti-
isomer and iodide ions are relatively weaker than those of the
syn-isomer. Furthermore, the changes of chemical shifts above
lead us to suggest that conformational changes occur in the
isomers upon interaction with the iodide anions, that is, local
induced-fit conformational changes happen.48
In order to further study the binding affinity of the two
receptors to iodide ions, during the titration of TBAI concen-
trations with different equivalence ratios, the changes in the
UV-visible absorption and fluorescence spectra of the two
receptors in CH2Cl2 for anions were monitored. As shown in
Fig. 4a and b, when IÀ is continuously added, the absorption
bands of syn-isomer and anti-isomer are significantly
enhanced, indicating that there are effective bonds between
the two receptors and IÀ. The UV-visible absorption spectra of
FÀ, ClÀ, and BrÀ at 240 nm show less changes, especially for FÀ
and ClÀ (Fig. S13–S18, ESI†), compared with that of IÀ, indicat-
ing that the interactions between syn-/anti-isomers with FÀ,
ClÀ, and BrÀ are relatively smaller. Compared with the
syn-isomer, the UV-visible absorption spectra of the anti-
isomer show new peaks at around 250 nm, which is coinciden-
tally close to the peak position of the syn-isomer corresponding
wavelength when there is a large excess of iodide ions, which
indicates that conformational changes of the anti-isomer follow
the initial binding step to optimize the complexes between the
isomers and iodide ions, that is, once the anti-isomer is
selected by an iodide ion, local induced-fit conformational
changes are also necessary to adjust the host to be perfectly
complementary to the guest.49
Fig. 3 (i) Changes of 1H NMR (400 MHz, CD2Cl2, 25 1C) of solutions of
syn-isomer and TBAI at different concentrations: (A) syn-isomer, (N) TBAI,
and equimolar solutions with concentrations of (B) 0.36, (C) 0.81, (D) 1.43,
(E) 2.35, (F) 3.40, (G) 4.87, (H) 6.39, (I) 7.65, (J) 9.15, (k) 10.52, (L) 12.70, and
(M) 13.48 equivalents. (ii) Changes of 1H NMR (400 MHz, CD2Cl2, 25 1C) of
solutions of anti-isomer TBAI at different concentrations: (a) anti-isomer,
(n) TBAI, and equimolar solutions with concentrations of (b) 0.20, (c) 0.75,
(d) 1.44, (e) 2.86, (f) 4.71, (g) 5.06, (h) 6.37, (j) 8.00, (k) 8.88, and (l) 11.00
equivalents.
According to the linear expression of Benesi–Hildebrand,50
the change of [1/(A À A0)] and 1/[IÀ] measured at 240 nm is
linear (Rsyn = 0.99102, Ranti = 0.99614),51,52 which indicates the
formation of 1 : 1 complexes between IÀ and the isomers, and
the association constants (K) of the complexes are determined,
Ksyn = (2.422 Æ 0.902) Â 104, and Kanti = (2.168 Æ 0.445) Â 103
(Fig. S19–S22, ESI†), which indicates that both receptors have
strong binding power with IÀ in dichloromethane solution, and
internal hydrogen atoms of the syn-isomer. The non-covalent the binding ability of syn-isomer with iodide ions is greater
bond reduces the density of internal aryl electrons, causing the than that of the anti-isomer with iodide ions. The fluorescence
N–H peak to shift to a low field. At the same time, after adding emission spectra also prove the response of the two receptors to
TBAI to the syn-isomer solution, the protons k, h, and f show a iodide anions (Fig. 4c and d). After adding TBAI to the syn-
slight displacement to the low field, while the protons a and b isomer and anti-isomer solutions, the fluorescence emission
move to the high field, which confirms the interaction between intensity decreases. However, in the entire halogen anion
the anions and the receptors. For the anti-isomer (Fig. 3ii), (FÀ, ClÀ, BrÀ, IÀ) fluorescence spectrum titration processes
when 4.71 equivalents of IÀ are added, the N–H peak of (Fig. S23–S28, ESI†), only the fluorescence emission intensity
carbazole only shifts to the low field by +0.25 ppm. When the changes, no peak position changes, and no new fluorescence
concentration of IÀ is increased to 11.00 equivalents, the N–H emission peak appears, which indicates that photoinduced
peak is located at 8.90 ppm. The NH peak of the anti-isomer electron transfer between the halogen anions and the isomers
experiences a smaller shift to the low field than that of the occurs.53,54 When IÀ content continues to increase, the fluores-
syn-isomer, and the protons k, a, and b peaks of anti-isomer are cence emission intensity of syn-isomer at 385.5 nm and 400 nm
not shifted, which indicates stronger interactions between the continues to decrease, and at 15 equivalents, 84.6% is
NH protons of syn-isomer and iodide ions. It can be reasonably quenched. Compared with IÀ, the quenching values of the
This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2021
New J. Chem., 2021, 45, 6796–6802
| 6799

View Article Online
NJC
Paper
Fig. 4 Upon addition of TBAI: (a) UV-Vis spectra of syn-isomer (10 mM) in CH2Cl2; (b) UV-Vis spectra of anti-isomer (10 mM) in CH2Cl2; (c) fluorescence
spectra of syn-isomer (10 mM) in CH2Cl2 (excitation wavelength: 230 nm); (d) fluorescence spectra of anti-isomer (10 mM) in CH2Cl2 (excitation
wavelength: 230 nm). The illustration shows the nonlinear fitting.
other three halogen anions (FÀ, ClÀ, BrÀ) are 6%, 16% and boat conformations, which can provide an ideal size for the
23%, respectively (Fig. S29, ESI†). Similarly, as IÀ content combination of iodide ions. By solving the association
continues to increase, the fluorescence emission intensity of constants, we have found that the interactions between the
anti-isomer at 380.5 nm and 396.5 nm also continues to anti-isomers and iodide ions are relatively weaker than those
decrease, and at 15 equivalents, it is quenched by 87.2%. in the syn-isomers, and the syn-isomers have much better
Compared with IÀ, the quenching values of the other three recognition selectivity for IÀ in CH2Cl2 than the anti-isomers.
halogen anions (FÀ, ClÀ, BrÀ) are 25.2%, 19.4% and 30.8%, According to the results of the theoretical calculations,
respectively (Fig. S30, ESI†). These results indicate that the syn/anti configurations bring about different orientations of
interactions are stronger between the two receptors and IÀ than the alkyl chains, leading to the larger steric hindrance of the
the other three halogen anions (FÀ, ClÀ, BrÀ), and the ability of anti-isomers to hinder the combination with iodide ions. The
these two isomers to recognize iodide ions is stronger than the introduction of non-covalent bonds and syn configurations
other three halogen anions (FÀ, ClÀ, BrÀ), which is consistent with relatively smaller steric hindrance can enhance the
with the conclusion of UV-Vis absorption titration.
binding between the isomers and the iodide anions, and it
is reasonable to infer that a local induced fit mechanism
follows a conformational selection in the recognition, which
can help to understand these two dominant binding mechan-
isms in molecular recognition and have a certain reference
value for designing better anion receptors.
Conclusions
In summary, we synthesized two shape-persistent macro-
cycles of syn/anti configurations, and studied their interac-
tions with halogen anions. Both the isomers show the
colorimetric and fluorescence recognition towards iodide
anions in dichloromethane solution. 1H NMR titration,
UV-Vis absorption and fluorescence spectroscopy studies
were used to prove the recognition. The crystal structure
Conflicts of interest
shows that the molecules in the syn-isomers reveal concave There are no conflicts to declare.
This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2021
6800
| New J. Chem., 2021, 45, 6796–6802

View Article Online
Paper
NJC
´˜
19 S. Ibanez and E. Peris, Angew. Chem., Int. Ed., 2020, 59,
Acknowledgements
6860–6865.
The authors would like to thank Associate Professor Yang Lei
for his helpful advice on the theoretical calculations in this
paper. The project was supported by the National Natural
Science Foundation of China (Grant No. 62074081), the Natural
Science Foundation of the Jiangsu Higher Education Institu-
tions of China (Grant No. 18KJA510003), the Synergetic Innova-
tion Centre for Organic Electronics and Information Displays
and the Priority Academic Program Development of Jiangsu
Higher Education Institutions (PAPD).
20 M. Y. Zhao, D. X. Wang and M. X. Wang, J. Org. Chem., 2018,
83, 1502–1509.
21 Q.-H. Guo, Z.-D. Fu, L. Zhao and M.-X. Wang, Angew. Chem.,
Int. Ed., 2014, 53, 13548–13552.
22 M. Lafosse, E. Cartier, K. Solmont, J. Rivollier, D. Azazna,
P. Thuery, Y. Boulard, A. Gontier, J. B. Charbonnier,
B. Kuhnast and M. P. Heck, Org. Lett., 2020, 22, 3099–3103.
23 M. Kandrnalova, Z. Kokan, V. Havel, M. Necas and
V. Sindelar, Angew. Chem., Int. Ed., 2019, 131, 18350–18353.
24 H. F. Sleem, L. N. Dawe and P. E. Georghiou, Tetrahedron
Lett., 2013, 54, 3444–3448.
25 H. F. Sleem, L. N. Dawe and P. E. Georghiou, New J. Chem.,
2012, 36, 2451–2455.
Notes and references
26 B. Datta, A. Roy and M. N. Roy, J. Chem. Sci., 2017, 129,
579–587.
27 A. F. D. de Namor and R. Khalife, Phys. Chem. Chem. Phys.,
2010, 12, 753–760.
28 D. J. Cram, Angew. Chem., Int. Ed. Engl., 1986, 25,
1039–1057.
1 J. W. Jones, L. N. Zakharov, A. L. Rheingold and
H. W. Gibson, J. Am. Chem. Soc., 2002, 124, 13378–13379.
2 S. Sun, X. Y. Hu, D. Z. Chen, J. B. Shi, Y. P. Dong, C. Lin,
Y. Pan and L. Y. Wang, Polym. Chem., 2013, 4, 2224–2229.
3 X. Ji, Y. Yao, J. Li, X. Yan and F. Huang, J. Am. Chem. Soc.,
2013, 135, 74–77.
29 X. P. Wang, F. Jia, L. P. Yang, H. Zhou and W. Jiang, Chem.
Soc. Rev., 2020, 49, 4176–4188.
4 J. Zhao, D. Yang, Y. X. Zhao, X. J. Yang, Y. Y. Wang and
B. Wu, Angew. Chem., Int. Ed., 2014, 53, 6632–6636.
5 C. M. Davis, K. Ohkubo, A. D. Lammer, D. S. Kim,
Y. Kawashima, J. L. Sessler and S. Fukuzumi, Chem. Commun.,
2015, 51, 9789–9792.
6 S. K. Ko, S. K. Kim, A. Share, V. M. Lynch, J. Park,
W. Namkung, W. Van Rossom, N. Busschaert, P. A. Gale,
J. L. Sessler and I. Shin, Nat. Chem., 2014, 6, 885–892.
7 M. Wenzel, J. R. Hiscock and P. A. Gale, Chem. Soc. Rev.,
2012, 41, 480–520.
30 L. Wang, G. W. Zhang, C. J. Ou, L. H. Xie, J. Y. Lin, Y. Y. Liu
and W. Huang, Org. Lett., 2014, 16, 1748–1751.
31 Q. Y. Feng, Y. L. Han, M. N. Yu, B. Li, Y. Wei, L.-H. Xie and
W. Huang, Chin. J. Polym. Sci., 2017, 35, 87–97.
32 G. W. Zhang, Y. Wei, J. S. Wang, Y. Y. Liu, L. H. Xie, L. Wang,
B. Y. Ren and W. Huang, Mater. Chem. Front., 2017, 1,
455–459.
33 D. Q. Lin, Y. Wei, A. Z. Peng, H. Zhang, C. X. Zhong, D. Lu,
H. Zhang, X. P. Zheng, L. Yang, Q. Y. Feng, L. H. Xie and
W. Huang, Nat. Commun., 2020, 11, 1756.
8 P. A. Gale, E. N. W. Howe, X. Wu and M. J. Spooner,
Coord. Chem. Rev., 2018, 375, 333–372.
34 D. J. Cram, Angew. Chem., Int. Ed. Engl., 1986, 25,
1039–1057.
9 P. D. Beer and P. A. Gale, Angew. Chem., Int. Ed., 2001, 40,
486–516.
35 B. Dietrich, M. W. Hosseini, J. M. Lehn and R. B. Sessions,
J. Am. Chem. Soc., 1981, 103, 1282–1283.
10 R. Sakai, N. Sakai, T. Satoh, W. Li, A. Zhang and T. Kakuchi,
Macromolecules, 2011, 44, 4249–4257.
36 Y. Q. Zhang, Y. J. Fan, S. S. Wang, Y. L. Tan, X. C. Shen and
Z. J. Shi, Chin. J. Chem., 2012, 30, 1163–1167.
37 J. L. Sessler and E. Tomat, Acc. Chem. Res., 2007, 40,
371–379.
11 V. Amendola, L. Fabbrizzi and L. Mosca, Chem. Soc. Rev.,
2010, 39, 3889–3915.
12 N. Busschaert, C. Caltagirone, W. V. Rossom and P. A. Gale,
Chem. Rev., 2015, 115, 8038–8155.
38 A. L. Allred, J. Inorg. Nucl. Chem., 1961, 17, 215–221.
39 C. N. Carroll, J. J. Naleway, M. M. Haley and D. W. Johnson,
Chem. Soc. Rev., 2010, 39, 3875–3888.
40 K. J. Chang, D. Moon, M. S. Lah and K. S. Jeong, Angew.
Chem., Int. Ed., 2005, 44, 7926–7929.
13 Y. C. Horng, P. S. Huang, C. C. Hsieh, C. H. Kuo and
T. S. Kuo, Chem. Commun., 2012, 48, 8844–8846.
14 C. J. Pedersen, Angew. Chem., Int. Ed. Engl., 1988, 27,
1021–1027.
15 C. A. Ilioudis, D. A. Tocher and J. W. Steed, J. Am. Chem. Soc.,
2004, 126, 12395–12402.
41 N. K. Kim, K. J. Chang, D. Moon, M. S. Lah and K. S. Jeong,
Chem. Commun., 2007, 3401–3403.
16 H. Gregolinska, M. Majewski, P. I. Chmielewski,
J. Gregolinski, A. Chien, J. W. Zhou, Y. L. Wu, Y. J. Bae, 42 H. G. Jeon, M. J. Kim and K. S. Jeong, Org. Biomol. Chem.,
M. R. Wasielewski, P. M. Zimmerman and M. Stepien, J. Am.
Chem. Soc., 2018, 140, 14474–14480.
17 H. T. Z. Zhu, B. B. Shi, K. X. Chen, P. F. Wei, D. Y. Xia,
2014, 12, 5464–5468.
43 A. Adam, S. Mehrparvar and G. Haberhauer, Beilstein J. Org.
Chem., 2019, 15, 1534–1544.
J. H. Mondal and F. H. Huang, Org. Lett., 2016, 18, 44 B. Das, J. N. McPherson and S. B. Colbran, Coord. Chem.
5054–5057. Rev., 2018, 363, 29–56.
´˜
18 S. Ibanez and E. Peris, Angew. Chem., Int. Ed., 2019, 58, 45 Y. Q. Wang, Y. J. Kim and M. Lee, Angew. Chem., Int. Ed.,
6693–6697. 2016, 55, 13122–13126.
This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2021
New J. Chem., 2021, 45, 6796–6802
| 6801

View Article Online
NJC
Paper
46 A. Kim, R. Ali, S. H. Park, Y. H. Kim and J. S. Park, 51 C. Kar, A. Basu and G. Das, Tetrahedron Lett., 2012, 53,
Chem. Commun., 2016, 52, 11139–11142.
47 A. Bondi, J. Phys. Chem., 1964, 68, 441–451.
48 A. Cembran, J. Kim, J. L. Gao and G. Veglia, Phys. Chem.
Chem. Phys., 2014, 16, 6508–6518.
49 H. Huang, L. Yang, A. Facchetti and T. J. Marks, Chem. Rev.,
2017, 117, 10291–10318.
4754–4757.
52 V. S. Bryantsev and B. P. Hay, J. Am. Chem. Soc., 2005, 127,
8282–8283.
53 A. P. D. Silva, H. Q. N. Gunaratne, T. Gunnlaugsson,
A. J. M. Huxley, C. P. McCoy, J. T. Rademacher and
T. E. Rice, Chem. Rev., 1997, 97, 1515–1566.
50 X. B. Yang, B. X. Yang, J. F. Ge, Y. J. Xu, Q. F. Xu, J. Liang and 54 E. Beilis, Y. Horowitz, A. Givon, G. A. Somorjai, H. Cohen
J. M. Lu, Org. Lett., 2011, 13, 2710–2713.
and S. Richter, J. Phys. Chem. C, 2017, 121, 9579–9586.
This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2021
6802
| New J. Chem., 2021, 45, 6796–6802