Citation: Yang Ling, Zhao Wei, Che Yan-Ke, Wang Ying, Jiang Hua. Influence of terminal substituents on the halide anion binding of foldamer-based receptors[J]. Chinese Chemical Letters, ;2017, 28(8): 1659-1662. doi: 10.1016/j.cclet.2017.06.006 shu

Influence of terminal substituents on the halide anion binding of foldamer-based receptors

Yang Ling ^a,c ,
Zhao Wei ^a,c ,
Che Yan-Ke ^a,, ,
Wang Ying ^b,, ,
Jiang Hua ^a,b,,

a.
Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Photochemistry, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China
b.
College of Chemistry, Beijing Normal University, Beijing 100875, China
c.
University of Chinese Academy of Sciences, Beijing 100049, China

Corresponding author: Che Yan-Ke, ykche@iccas.ac.cn Wang Ying, ywang1@bnu.edu.cn Jiang Hua, jiangh@bnu.edu.cn
Received Date: 17 April 2017
Revised Date: 10 May 2017
Accepted Date: 2 June 2017
Available Online: 8 August 2017

Figures(5)

Foldamers 1-4 incorporating different terminal substituents have been designed and synthesized for binding halide anions. ¹H NMR titration experiments carried out in DMSO-d₆/CDCl₃ (15/85, v/v) demonstrated that the short oligo(aryltriazole)s backbone 1 could not bind halide anions unless that amide H-bond donors were incorporated at the termini of the oligomer. Terminal substituents on oligo(aryltriazoleamide)s foldamers 2-4 display a considerable influence on the binding affinities of the foldamers for halide anions. Large steric hindrance of the terminal substituents was found to be unfavorable for binding halide anions, but aromatic π-π interactions between two terminal substituents are capable of stabilizing the conformation of foldamers thus giving rise to an enhancement in the binding strengths. However, the terminal substituents were found to hardly affect the binding selectivity in the studied cases.
- Anion binding,
- Triazole,
- Recognition,
- Receptors,
- Terminal substituents
1. [1]
  Beer P.D., Gale P.A.. Anion recognition and sensing:the state of the art and future perspectives[J]. Angew. Chem. Int. Ed., 2001,40:486-516. doi: 10.1002/1521-3773(20010202)40:3<>1.0.CO;2-A
2. [2]
  Sessler J.L., Camiolo S., Gale P.A.. Pyrrolic and polypyrrolic anion binding agents[J]. Coord. Chem. Rev., 2003,240:17-55. doi: 10.1016/S0010-8545(03)00023-7
3. [3]
  Amendola V., Esteban-Gmez D., Fabbrizzi L., Licchelli M.. What anions do to NH-containing receptors[J]. Acc. Chem. Res., 2006,39:343-353. doi: 10.1021/ar050195l
4. [4]
  Caltagirone C., Gale P.A.. Anion receptor chemistry:highlights from 2007[J]. Chem. Soc. Rev., 2009,38:520-563. doi: 10.1039/B806422A
5. [5]
  Kubik S.. Amino acid containing anion receptors[J]. Chem. Soc. Rev., 2009,38:585-605. doi: 10.1039/B810531F
6. [6]
  Wenzel M., Hiscock J.R., Gale P.A.. Anion receptor chemistry:highlights from 2010[J]. Chem. Soc. Rev., 2012,41:480-520. doi: 10.1039/C1CS15257B
7. [7]
  Evans N.H., Beer P.D.. Advances in anion supramolecular chemistry:from recognition to chemical applications[J]. Angew. Chem. Int. Ed., 2014,53:11716-11754. doi: 10.1002/anie.201309937
8. [8]
  Hill D.J., Mio M.J., Prince R.B., Hughes T.S., Moore J.S.. A field guide to foldamers[J]. Chem. Rev, 2001,101:3893-4011. doi: 10.1021/cr990120t
9. [9]
  S. Hecht, I. Huc, Foldamers: Structures, Properties, and Applications, WileyVCH, Weinheim, 2007.
10. [10]
  Juwarker H., Suk J.M., Jeong K.S.. Foldamers with helical cavities for binding complementary guests[J]. Chem. Soc. Rev., 2009,38:3316-3325. doi: 10.1039/b909034g
11. [11]
  Juwarker H., Jeong K.S.. Anion-controlled foldamers[J]. Chem. Soc. Rev, 2010,39:3664-3674. doi: 10.1039/b926162c
12. [12]
  Chang K.J., Moon D., Lah M.S., Jeong K.S.. Indole-based macrocycles as a class of receptors for anions[J]. Angew. Chem. Int. Ed., 2005,44:7926-7929. doi: 10.1002/(ISSN)1521-3773
13. [13]
  Chang K.J., Kang B.N., Lee M.H., Jeong K.S.. Oligoindole-based foldamers with a helical conformation induced by chloride[J]. J. Am. Chem. Soc., 2005,127:12214-12215. doi: 10.1021/ja0547984
14. [14]
  Juwarker H., Lenhardt J.M., Pham D.M., Craig S.L.. 1, 2, 3-Triazole CH…Cl contacts guide anion binding and concomitant folding in 1, 4-diaryl triazole oligomers[J]. Angew. Chem. Int. Ed., 2008,47:3740-3743. doi: 10.1002/(ISSN)1521-3773
15. [15]
  Amendola V., Fabbrizzi L., Mosca L.. Anion recognition by hydrogen bonding:urea-based receptors[J]. Chem. Soc. Rev., 2010,39:3889-3915. doi: 10.1039/b822552b
16. [16]
  Bondy C.R., Loeb S.J.. Amide based receptors for anions[J]. Coord. Chem. Rev., 2003,240:77-99. doi: 10.1016/S0010-8545(02)00304-1
17. [17]
  Zhang D.W., Zhao X., Hou J.L., Li Z.T.. Aromatic amide foldamers:structures, properties, and functions[J]. Chem. Rev., 2012,112:5271-5316. doi: 10.1021/cr300116k
18. [18]
  Chmielewski M.J., Charon M., Jurczak J.. 1, 8-Diamino-3, 6-dichlorocarbazole:a promising building block for anion receptors[J]. Org. Lett., 2004,6:3501-3504. doi: 10.1021/ol048661e
19. [19]
  Bryantsev V.S., Hay B.P.. Are C-H groups significant hydrogen bonding sites in anion Receptors? Benzene complexes with Cl^- NO₃^-, and ClO₄^-[J]. J. Am. Chem. Soc., 2005,127:8282-8283. doi: 10.1021/ja0518272
20. [20]
  Bates G.W., Triyanti , Light M.E., Albrecht M., Gale P.A.. 2, 7-Functionalized indoles as receptors for anions[J]. J. Org. Chem., 2007,72:8921-8927. doi: 10.1021/jo701702p
21. [21]
  Bates G.W., Gale P.A., Light M.E.. Isophthalamides and 2, 6-dicarboxamidopyridines with pendant indole groups:a 'twisted' binding mode for selective fluoride recognition[J]. Chem. Commun., 2007,21:2121-2123.
22. [22]
  Kim U.I., Suk J.M., Naidu V.R., Jeong K.S.. Folding and anion-binding properties of fluorescent oligoindole foldamers[J]. Chem. Eur. J., 2008,14:11406-11414. doi: 10.1002/chem.200801713
23. [23]
  Zhang D.W., Zhao X., Li Z.T.. Aromatic amide and hydrazide foldamer-based responsive host-guest Systems[J]. Acc. Chem. Res., 2014,47:1961-1970. doi: 10.1021/ar5000242
24. [24]
  Lee S., Hua Y., Park H., Flood A.H.. Intramolecular hydrogen bonds preorganize an aryl-triazole receptor into a crescent for chloride binding[J]. Org. Lett., 2010,12:2100-2102. doi: 10.1021/ol1005856
25. [25]
  Lee S., Hua Y., Flood A.H.. b-Sheet-like hydrogen bonds interlock the helical turns of a photoswitchable foldamer to enhance the binding and release of chloride[J]. J. Org. Chem., 2014,79:8383-8396. doi: 10.1021/jo501595k
26. [26]
  Haridas V., Sahu S., Praveen Kumar P.P.. Triazole-based chromogenic and nonchromogenic receptors for halides[J]. Tetrahedron Lett., 2011,52:6930-6934. doi: 10.1016/j.tetlet.2011.10.066
27. [27]
  Haridas V., Sahu S., Venugopalan P.. Halide binding and self-assembling behavior of triazole-based acyclic and cyclic molecules[J]. Tetrahedron, 2011,67:727-733. doi: 10.1016/j.tet.2010.11.078
28. [28]
  Wang Y., Li F., Han Y., Wang F.Y., Jiang H.. Folding and aggregation of cationic oligo(aryl-triazole)s in aqueous solution[J]. Chem. Eur. J., 2009,15:9424-9433. doi: 10.1002/chem.v15:37
29. [29]
  Wang Y., Bie F.S., Jiang H.. Controlling binding affinities for anions by a photoswitchable foldamer[J]. Org. Lett., 2010,12:3630-3633. doi: 10.1021/ol1014043
30. [30]
  Wang Y., Xiang J., Jiang H.. Halide-guided oligo(aryl-triazole-amide)s foldamers:receptors for multiple halide ions[J]. Chem. Eur. J., 2011,17:613-619. doi: 10.1002/chem.201001560
31. [31]
  Shang J., Gallagher N.M., Bie F.S.. Aromatic triazole foldamers induced by C-H…X (X=F, Cl) intramolecular hydrogen bonding[J]. J. Org. Chem., 2014,79:5134-5144. doi: 10.1021/jo500582c
32. [32]
  Shang J., Si W., Zhao W.. Preorganized aryltriazole foldamers as effective transmembrane transporters for chloride anion[J]. Org. Lett., 2014,16:4008-4011. doi: 10.1021/ol501772v
33. [33]
  Zhao W., Wang Y., Shang J., Che Y.K., Jiang H.. Acid/base-mediated uptake and release of halide anions with a preorganized aryl-triazole foldamer[J]. Chem. Eur. J., 2015,21:7731-7735. doi: 10.1002/chem.v21.21
34. [34]
  Zhao W., Huang F., Wang Y.. Aryl-triazole foldamers with ethynyl spacers as effective receptors for halides and oxyanions[J]. Tetrahedron Lett., 2016,15:1691-1694.
35. [35]
  Shang J., Zhao W., Li X.C., Wang Y., Jiang H.. Aryl-triazole foldamers incorporating a pyridinium motif for halide anion binding in aqueous media[J]. Chem. Commun., 2016,52:4505-4508. doi: 10.1039/C5CC10422J
36. [36]
  Wang Y., Zhao W., Bie F.S.. Ruthenium(Ⅱ) complexes of aryl triazole foldamers as receptors for anions[J]. Chem. Eur. J., 2016,22:5233-5242. doi: 10.1002/chem.201504910
37. [37]
  Juwarker H., Lenhardt J.M., Pham D.M., Craig S.L.. 1, 23-Triazole CH…Cl contacts guide anion binding and concomitant folding in 1, 4-diaryl triazole oligomers[J]. Angew. Chem. Int. Ed., 2008,47:3740-3743. doi: 10.1002/(ISSN)1521-3773
38. [38]
  Saraogi I., Hamilton A.D.. Recent advances in the development of aryl-based foldamers[J]. Chem. Soc. Rev., 2009,38:1726-1743. doi: 10.1039/b819597h
39. [39]
  Hua Y., Flood A.H.. Click chemistry generates privileged CH hydrogen-bonding triazoles:the latest addition to anion supramolecular chemistry[J]. Chem. Soc. Rev., 2010,39:1262-1271. doi: 10.1039/b818033b
40. [40]
  Qiao B., Sengupta A., Liu Y.. Electrostatic and allosteric cooperativity in ion-pair binding:a quantitative and coupled experiment-theory study with aryl-triazole-ether Macrocycles[J]. J. Am. Chem. Soc., 2015,137:9746-9757. doi: 10.1021/jacs.5b05839
41. [41]
  M. J. Frisch, G. W. Trucks, H. B. Schlegel, et al. , Gaussian 03, Revision D. 02, Gaussian Inc. , Pittsburgh, PA, 2004.
42. [42]
  Hynes M.J.. EQNMR:a computer program for the calculation of stability constants from nuclear magnetic resonance chemical shift data[J]. J. Chem. Soc. Dalton Trans, 1993:311-312.
43. [43]
  Rostovtsev V.V., Green L.G., Fokin V.V., Sharpless K.B.. A stepwise Huisgen cycloaddition process:copper(Ⅰ)-catalyzed regioselective Ligation of azides and terminal alkynes[J]. Angew. Chem., 2002,114:2708-2711. doi: 10.1002/1521-3757(20020715)114:14<2708::AID-ANGE2708>3.0.CO;2-0
44. [44]
  Torn C.W., Christensen C., Meldal M.. Peptidotriazoles on solid phase:[12, 3]-triazoles by regiospecific copper(Ⅰ)-catalyzed 1, 3-dipolar cycloadditions of terminal alkynes to azides[J]. J. Org. Chem., 2002,67:3057-3064. doi: 10.1021/jo011148j
45. [45]
  Li Y., Flood A.H.. trong, size-selective, and electronically tunable C-H^… halide binding with steric control over aggregation from synthetically modular, shape-persistent [з₄] triazolophanes[J]. J. Am. Chem. Soc., 2008,130:12111-12122. doi: 10.1021/ja803341y
1. [1]
  Fang-Yuan Chen , Wen-Chao Geng , Kang Cai , Dong-Sheng Guo . Molecular recognition of cyclophanes in water. Chinese Chemical Letters, 2024, 35(5): 109161-. doi: 10.1016/j.cclet.2023.109161
2. [2]
  Caihong Mao , Yanfeng He , Xiaohan Wang , Yan Cai , Xiaobo Hu . Synthesis and molecular recognition characteristics of a tetrapodal benzene cage. Chinese Chemical Letters, 2024, 35(8): 109362-. doi: 10.1016/j.cclet.2023.109362
3. [3]
  Cheng-Da Zhao , Huan Yao , Shi-Yao Li , Fangfang Du , Li-Li Wang , Liu-Pan Yang . Amide naphthotubes: Biomimetic macrocycles for selective molecular recognition. Chinese Chemical Letters, 2024, 35(4): 108879-. doi: 10.1016/j.cclet.2023.108879
4. [4]
  Shiqi Xu , Zi Ye , Shuang Shang , Fengge Wang , Huan Zhang , Lianguo Chen , Hao Lin , Chen Chen , Fang Hua , Chong-Jing Zhang . Pairs of thiol-substituted 1,2,4-triazole-based isomeric covalent inhibitors with tunable reactivity and selectivity. Chinese Chemical Letters, 2024, 35(7): 109034-. doi: 10.1016/j.cclet.2023.109034
5. [5]
  Yue Mao , Zhonghang Chen , Tiankai Sun , Wenyue Cui , Peng Cheng , Wei Shi . Luminescent coordination polymers with mixed carboxylate and triazole ligands for rapid detection of chloroprene metabolite. Chinese Journal of Structural Chemistry, 2024, 43(9): 100353-100353. doi: 10.1016/j.cjsc.2024.100353
6. [6]
  Zhimin Sun , Xin-Hui Guo , Yue Zhao , Qing-Yu Meng , Li-Juan Xing , He-Lue Sun . Dynamically switchable porphyrin-based molecular tweezer for on−off fullerene recognition. Chinese Chemical Letters, 2024, 35(6): 109162-. doi: 10.1016/j.cclet.2023.109162
7. [7]
  Chuan-Zhi Ni , Ruo-Ming Li , Fang-Qi Zhang , Qu-Ao-Wei Li , Yuan-Yuan Zhu , Jie Zeng , Shuang-Xi Gu . A chiral fluorescent probe for molecular recognition of basic amino acids in solutions and cells. Chinese Chemical Letters, 2024, 35(10): 109862-. doi: 10.1016/j.cclet.2024.109862
8. [8]
  Weichen WANG , Chunhua GONG , Junyong ZHANG , Yanfeng BI , Hao XU , Jingli XIE . Construction of two metal-organic frameworks by rigid bis(triazole) and carboxylate mixed-ligands and their catalytic properties for CO₂ cycloaddition reaction. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1377-1386. doi: 10.11862/CJIC.20230415
9. [9]
  Zhen Dai , Linzhi Tan , Yeyu Su , Kerui Zhao , Yushun Tian , Yu Liu , Tao Liu . Site-specific incorporation of reduction-controlled guest amino acids into proteins for cucurbituril recognition. Chinese Chemical Letters, 2024, 35(5): 109121-. doi: 10.1016/j.cclet.2023.109121
10. [10]
  Yuanjiao Liu , Xiaoyang Zhao , Songyao Zhang , Yi Wang , Yutuo Zheng , Xinrui Miao , Wenli Deng . Site-selection and recognition of aromatic carboxylic acid in response to coronene and pyridine derivative. Chinese Chemical Letters, 2024, 35(8): 109404-. doi: 10.1016/j.cclet.2023.109404
11. [11]
  Huan Yao , Jian Qin , Yan-Fang Wang , Song-Meng Wang , Liu-Huan Yi , Shi-Yao Li , Fangfang Du , Liu-Pan Yang , Li-Li Wang . Ultra-highly selective recognition of nucleosides over nucleotides by rational modification of tetralactam macrocycle and its application in enzyme assay. Chinese Chemical Letters, 2024, 35(6): 109154-. doi: 10.1016/j.cclet.2023.109154
12. [12]
  Yunjia Jiang , Lingyao Wang , Yuanbin Zhang . Anion pillared MOFs for challenging hydrocarbon separations. Chinese Journal of Structural Chemistry, 2024, 43(11): 100374-100374. doi: 10.1016/j.cjsc.2024.100374
13. [13]
  Lu LIU , Huijie WANG , Haitong WANG , Ying LI . Crystal structure of a two-dimensional Cd(Ⅱ) complex and its fluorescence recognition of p-nitrophenol, tetracycline, 2, 6-dichloro-4-nitroaniline. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1180-1188. doi: 10.11862/CJIC.20230489
14. [14]
  Wu-Jian Long , Yang Yu , Chuang He . A novel and promising engineering application of carbon dots: Enhancing the chloride binding performance of cement. Chinese Chemical Letters, 2024, 35(6): 108943-. doi: 10.1016/j.cclet.2023.108943
15. [15]
  Zhili Li , Qijun Wo , Dongdong Huang , Dezhong Zhou , Lei Guo , Yeqing Mao . Improving gene transfection efficiency of highly branched poly(β-amino ester)s through the in-situ conversion of inactive terminal groups. Chinese Chemical Letters, 2024, 35(8): 109737-. doi: 10.1016/j.cclet.2024.109737
16. [16]
  Xiaoyao Ma , Jinling Zhang , Ge Fang , He Gao , Jie Gao , Li Fu , Yuanyuan Hou , Gang Bai . Förster resonance energy transfer reveals phillygenin and swertiamarin concurrently target AKT on different binding domains to increase the anti-inflammatory effect. Chinese Chemical Letters, 2024, 35(5): 108823-. doi: 10.1016/j.cclet.2023.108823
17. [17]
  Jing JIN , Zhuming GUO , Zhiyin XIAO , Xiujuan JIANG , Yi HE , Xiaoming LIU . Tuning the stability and cytotoxicity of fac-[Fe(CO)₃I₃]^- anion by its counter ions: From aminiums to inorganic cations. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 991-1004. doi: 10.11862/CJIC.20230458
18. [18]
  Hong-Jin Liao , Zhu Zhuo , Qing Li , Yoshihito Shiota , Jonathan P. Hill , Katsuhiko Ariga , Zi-Xiu Lu , Lu-Yao Liu , Zi-Ang Nan , Wei Wang , You-Gui Huang . A new class of crystalline X-ray induced photochromic materials assembled from anion-directed folding of a flexible cation. Chinese Chemical Letters, 2024, 35(8): 109052-. doi: 10.1016/j.cclet.2023.109052
19. [19]
  Pu Zhang , Xiang Mao , Xuehua Dong , Ling Huang , Liling Cao , Daojiang Gao , Guohong Zou . Two UV organic-inorganic hybrid antimony-based materials with superior optical performance derived from cation-anion synergetic interactions. Chinese Chemical Letters, 2024, 35(9): 109235-. doi: 10.1016/j.cclet.2023.109235

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(589)
HTML views(5)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142