8. Hansen JG, Feeder N, Hamilton DG, Gunter MJ, Becher J, Sanders JKM (2000)
Macrocyclization and molecular interlocking via Mitsunobu alkylation: highlighting the role
of C–HÁ Á ÁO interactions in templating. Org Lett 2:449–452
9. Xue M, Yang Y, Chi X, Yan X, Huang F (2015) Development of pseudorotaxanes and
rotaxanes: from synthesis to stimuli-responsive motions to applications. Chem Rev
115:7398–7501
10. Dunitz JD, Seiler P (1974) 1,4,7,10,13,16-Hexaoxacyclooctadecane. Acta Crystallogr Sect B
30:2739–2741
11. Tamao K, Hayashi T, Ito Y, Shiro M (1992) Electronic and steric effects in pentacoordinate
anionic diorganotrifluorosilicates: x-ray structures and carbon-13 NMR studies for evaluation
of charge distribution in aryl groups on silicon. Organometallics 11:182–191
12. Buschmann H-J (1988) The influence of acetonitrile on complex formation of crown ethers
containing different donor atoms. J Solut Chem 17:277–286
13. Lamb JD, Izatt RM, Swain CS, Christensen JJ (1980) A systematic study of the effect
of macrocycle ring size and donor atom type on the log K, .DELTA.H, and T.DELTA.S
of reactions at 25.degree.C in methanol of mono- and divalent cations with crown ethers.
J Am Chem Soc 102:475–479
14. Takeda Y, Arima O (1985) Temperature dependence of walden product of 18-crown-6–k
+
complex in water. Bull Chem Soc Jpn 58:3403–3404
15. Izatt RM, Lamb JD, Izatt NE, Rossiter BE, Christensen JJ, Haymore BL (1979) A calorimetric
titration study of the reaction of several organic ammonium cations with 18-crown-6 in
methanol. J Am Chem Soc 101:6273–6276
16. Izatt RM, Terry RE, Haymore BL, Hansen LD, Dally NK, Avondet AG, Christensen JJ (1976)
Calorimetric titration study of the interaction of several uni- and bivalent cations with 15-crown5, 18-crown-6, and two isomers of dicyclohexo-18-crown-6 in aqueous solution at 25.degree.C
and .mu. = 0.1. J Am Chem Soc 98:7620–7626
17. Allwood BL, Spencer N, Shahriari-Zavareh H, Stoddart JF, Williams DJ (1987) Complexation
of paraquat by a bisparaphenylene-34-crown-10 derivative. J Chem Soc Chem Comm
14:1064–1066
18. Lestini E, Nikitin K, Müller-Bunz H, Fitzmaurice D (2008) Introducing negative charges into
bis-p-phenylene crown ethers: a study of bipyridinium-based [2]pseudorotaxanes and [2]
rotaxanes. Chem Eur J 14:1095–1106
19. (a) Umetani S, Sasaki T, Matsui M, Tsurubou S, Kimura T, Yoshid Z (1997) Complex formation
of metal ions with sulfonated crown ethers in water as ion size selective masking reagents. Anal
Sci 13:123–126; (b) Sasaki T, Umetani S, Matsui M, Tsurubou S, Kimura T, Yoshida Z (1998)
Complex formation of lanthanide ions with sulfonated crown ethers in aqueous solution. Bull
Chem Soc Jpn 71:371–377
20. Hoffart DJ, Tiburcio J, de la Torre A, Knight LK, Loeb SJ (2008) Cooperative ion–ion
interactions in the formation of interpenetrated molecules. Angew Chem Int Ed 47:97–101
21. Loeb SJ, Wisner JA (1998) A new motif for the self-assembly of [2]pseudorotaxanes; 1,2bis(pyridinium)ethane axles and [24]crown-8 ether wheels. Angew Chem Int Ed 37:
2838–2840
22. Sekine M, Matsuzaki J-I, Hata T (1985) Oligodeoxyribonucleotide synthesis by use of S,Sdiphenyl deoxyribonucleoside 3
0 -phosphorodithioates and bifunctional condensing reagents in
the phosphotriester approach. Tetrahedron 41:5279–5288
23. Chen L, Zhang Y-M, Liu Y (2012) Molecular binding behaviors between tetrasulfonated bis(mphenylene)-26-crown-8 and bispyridinium guests in aqueous solution. J Phys Chem B
116:9500–9506
24. Chen L, Zhang H-Y, Liu Y (2012) High affinity crown ether complexes in water: thermodynamic analysis, evidence of crystallography and binding of NAD
+ . J Org Chem 77:9766–9773
25. Chen L, Zhang Y-M, Wang L-H, Liu Y (2013) Molecular binding behaviors of pyromellitic and
naphthalene diimide derivatives by tetrasulfonated 1,5-dinaphtho-(3n+8)-crown-n (n = 8, 10)
in aqueous solution. J Org Chem 78:5357–5363
1 Water-Soluble Aromatic Crown Ethers
25
Macrocyclization and molecular interlocking via Mitsunobu alkylation: highlighting the role
of C–HÁ Á ÁO interactions in templating. Org Lett 2:449–452
9. Xue M, Yang Y, Chi X, Yan X, Huang F (2015) Development of pseudorotaxanes and
rotaxanes: from synthesis to stimuli-responsive motions to applications. Chem Rev
115:7398–7501
10. Dunitz JD, Seiler P (1974) 1,4,7,10,13,16-Hexaoxacyclooctadecane. Acta Crystallogr Sect B
30:2739–2741
11. Tamao K, Hayashi T, Ito Y, Shiro M (1992) Electronic and steric effects in pentacoordinate
anionic diorganotrifluorosilicates: x-ray structures and carbon-13 NMR studies for evaluation
of charge distribution in aryl groups on silicon. Organometallics 11:182–191
12. Buschmann H-J (1988) The influence of acetonitrile on complex formation of crown ethers
containing different donor atoms. J Solut Chem 17:277–286
13. Lamb JD, Izatt RM, Swain CS, Christensen JJ (1980) A systematic study of the effect
of macrocycle ring size and donor atom type on the log K, .DELTA.H, and T.DELTA.S
of reactions at 25.degree.C in methanol of mono- and divalent cations with crown ethers.
J Am Chem Soc 102:475–479
14. Takeda Y, Arima O (1985) Temperature dependence of walden product of 18-crown-6–k
+
complex in water. Bull Chem Soc Jpn 58:3403–3404
15. Izatt RM, Lamb JD, Izatt NE, Rossiter BE, Christensen JJ, Haymore BL (1979) A calorimetric
titration study of the reaction of several organic ammonium cations with 18-crown-6 in
methanol. J Am Chem Soc 101:6273–6276
16. Izatt RM, Terry RE, Haymore BL, Hansen LD, Dally NK, Avondet AG, Christensen JJ (1976)
Calorimetric titration study of the interaction of several uni- and bivalent cations with 15-crown5, 18-crown-6, and two isomers of dicyclohexo-18-crown-6 in aqueous solution at 25.degree.C
and .mu. = 0.1. J Am Chem Soc 98:7620–7626
17. Allwood BL, Spencer N, Shahriari-Zavareh H, Stoddart JF, Williams DJ (1987) Complexation
of paraquat by a bisparaphenylene-34-crown-10 derivative. J Chem Soc Chem Comm
14:1064–1066
18. Lestini E, Nikitin K, Müller-Bunz H, Fitzmaurice D (2008) Introducing negative charges into
bis-p-phenylene crown ethers: a study of bipyridinium-based [2]pseudorotaxanes and [2]
rotaxanes. Chem Eur J 14:1095–1106
19. (a) Umetani S, Sasaki T, Matsui M, Tsurubou S, Kimura T, Yoshid Z (1997) Complex formation
of metal ions with sulfonated crown ethers in water as ion size selective masking reagents. Anal
Sci 13:123–126; (b) Sasaki T, Umetani S, Matsui M, Tsurubou S, Kimura T, Yoshida Z (1998)
Complex formation of lanthanide ions with sulfonated crown ethers in aqueous solution. Bull
Chem Soc Jpn 71:371–377
20. Hoffart DJ, Tiburcio J, de la Torre A, Knight LK, Loeb SJ (2008) Cooperative ion–ion
interactions in the formation of interpenetrated molecules. Angew Chem Int Ed 47:97–101
21. Loeb SJ, Wisner JA (1998) A new motif for the self-assembly of [2]pseudorotaxanes; 1,2bis(pyridinium)ethane axles and [24]crown-8 ether wheels. Angew Chem Int Ed 37:
2838–2840
22. Sekine M, Matsuzaki J-I, Hata T (1985) Oligodeoxyribonucleotide synthesis by use of S,Sdiphenyl deoxyribonucleoside 3
0 -phosphorodithioates and bifunctional condensing reagents in
the phosphotriester approach. Tetrahedron 41:5279–5288
23. Chen L, Zhang Y-M, Liu Y (2012) Molecular binding behaviors between tetrasulfonated bis(mphenylene)-26-crown-8 and bispyridinium guests in aqueous solution. J Phys Chem B
116:9500–9506
24. Chen L, Zhang H-Y, Liu Y (2012) High affinity crown ether complexes in water: thermodynamic analysis, evidence of crystallography and binding of NAD
+ . J Org Chem 77:9766–9773
25. Chen L, Zhang Y-M, Wang L-H, Liu Y (2013) Molecular binding behaviors of pyromellitic and
naphthalene diimide derivatives by tetrasulfonated 1,5-dinaphtho-(3n+8)-crown-n (n = 8, 10)
in aqueous solution. J Org Chem 78:5357–5363
1 Water-Soluble Aromatic Crown Ethers
25