Supramolecular Chemistry
319
S.; Dey, J. Chem. Commun. 2009, 6997–6999; (c) Hwang,
I.; Jeon, W.S.; Kim, H.-J.; Kim, D.; Kim, H.; Selvapalam,
N.; Fujita, N.; Shinkai, S.; Kim, K. Angew. Chem., Int. Ed.
2007, 46, 210–213; (d) Shi, N.; Dong, H.; Yin, G.; Xu Z.;
Li, S. Adv. Funct. Mater. 2007, 17, 1837–1843; (e) Ghosh,
A.; Dey, J. Langmuir 2009, 25, 8466–8472; (f) Ajayaghosh,
A.; Praveen, V.K.; Vijayakumar, C. Chem. Soc. Rev. 2008,
37, 109–122; (g) Bhattacharya, S.; Samanta, S.K.
Langmuir 2009, 25, 8378–8381; (h) Lyon, L.A.; Meng,
Z.; Singh, N.; Sorrell, C.D.; John, A.S. Chem. Soc. Rev.
2009, 38, 865–874; (i) Koda, D.; Maruyama, T.;
Minakuchi, N.; Nakashima, K.; Goto, M. Chem. Commun.
2010, 46, 979–981; (j) Piepenbrock, M.-O.M.; Lloyd, G.O.;
Clarke, N.; Steed, J.W. Chem. Rev. 2010, 110, 1960–2004
and references cited there in.
of 1. The chloride salt of 1 (0.6 g, 0.8 mmol) was next
dissolved in MeOH (10 ml) and an aqueous solution of
NH4PF6 (0.262 g, 1.61 mmol) was added under hot
condition. After stirring the mixture for 30 min, the
precipitate was filtered. Repeated crystallisation of the
precipitate from petroleum ether afforded pure compound
1
1 in 74% yield (0.51 g, m.p. 1638C). H NMR (400 MHz,
CDCl3 containing few drops of DMSO-d6) d 9.88 (s, 1H),
9.38 (s, 1H), 9.20 (s, 1H), 8.30 (d, 1H, J ¼ 4 Hz), 8.19 (d,
1H, J ¼ 8 Hz), 7.91 (d, 2H, J ¼ 8 Hz), 7.69 (t, 1H,
J ¼ 8 Hz), 7.43 (d, 2H, J ¼ 8 Hz), 5.29 (s, 2H), 5.11 (s,
1H), 4.40 (m, 1H), 2.11 (m, 2H), 1.75–0.58 (m, 38H), 0.41
(s, 3H); 13C NMR (100 MHz, DMSO-d6) d 165.8, 162.3,
151.6, 145.2, 141.7, 139.8, 139.4, 139.0, 135.5, 127.7,
125.0, 122.5, 118.2, 75.9, 60.8, 56.0, 55.5, 49.3, 41,8, 37.4,
36.3, 36.0, 35.7, 35.6, 35.1, 31.2, 30.7, 27.7, 27.3, 27.1,
23.8, 23.1, 22.6, 22.3, 20.5, 18.8, 10.2 (one carbon in the
aliphatic region unresolved); FTIR (KBr, cm21): 3401,
2938, 2868, 1753, 1597, 1563, 1504; HR-MS (TOF MS
ESþ): C41H57N4O5PF6þ, (M-PF6) requires 685.4323 found
685.4378.
(6) (a) Ullman’s Encyclopedia of Industrial Chemistry, 6th ed.;
Wiley-VCH: New York, Germany, 1998; Krik, K.L.
Biochemistry of Halogens and Inorganic Halides; Plenum:
New York, 1991; (b) Rurack, K.; Resch-Genger, U. Chem.
Soc. Rev. 2002, 31, 116–127; (c) Sessler, J.L.; Gale, P.A.;
Cho, W.S.; Anion Receptor Chemistry; The Royel Society
of Chemistry: Cambridge, 2006.
(7) (a) van Esch, J.H.; Feringa, B.L. Angew. Chem., Int. Ed.
2000, 39, 2263–2266; (b) Estorff, L.P.; Hamilton, A. Chem.
Rev. 2004, 104, 1201–1218; (c) Ajayaghosh, A.; Praveen,
V.K. Acc. Chem. Res. 2007, 40, 664–656; (d) Sangeetha, N.
M.; Maitra, U. Chem. Soc. Rev. 2005, 34, 821–836; (e)
Hwang, I.; Jeon, W.S.; Kim, H.-J.; Kim, D.; Kim, H.;
Selvapalam, N.; Fujita, N.; Shinkai, S.; Kim, K. Angew.
Chem., Int. Ed. 2007, 46, 210–213; (f) George, M.; Weiss,
R.G. Acc. Chem. Res. 2006, 39, 489–497; (g) Danjo, H.;
Hirata, K.; Yoshigai, S.; Azumaya, I.; Yamaguchi, K. J. Am.
Chem. Soc. 2009, 131, 1638–1639.
(8) (a) Qu, Y.; Hua, J.L.; Tian, H. Org. Lett. 2010, 12, 3320–
3323; (b) Horowitz, H.S. J. Public Health Dent. 2003, 63,
3–8; (c) Singh, P.P.; Barjatiya, M.K.; Dhing, S.; Bhatnagar,
R.; Kothari, S.; Dhar, V. Urol. Res. 2001, 29, 238–244; (d)
Riggs, B.L. Bone and Mineral Research; Annual 2;
Elsevier: Amsterdam, 1984; pp 366–393; (e) Kleerekoper,
M. Endocrinol. Metab. Clin. North Am. 1998, 27, 441.
(9) (a) Yang, H.; Yi, T.; Zhou, Z.; Wu, J.; Xu, M.; Li, F.;
Huang, C.; Langmuir 2007, 23, 8224–8230; (b) Maeda, H.
Chem. Eur. J. 2008, 14, 11274–11282; (c) Piepenbrock, M.-
O.M.; Lloyd, G.O.; Clarke, N.; Steed, J.W. Chem. Rev.
2010, 110, 1960–2004; (d) Zhang, Y.-M.; Lin, Q.; Wei, T.-
B.; Qin, X.-P.; Li, Y. Chem. Commun. 2009, 6074–6076; (e)
Zhang, Y.; Jiang, S. Org. Biomol. Chem. 2012, 10, 6973–
6979; (f) Rajamalli, P.; Prasad, E. Soft Matter 2012, 8,
8896–8903; (h) Kim, T.H.; Kwon, N.Y.; Lee, T.S.
Tetrahedron Lett. 2010, 51, 5596–5600; (i) Xing, L.-B.;
Yang, B.; Wang, X.-J.; Wang, J.-J.; Chen, B.; Wu, Q.; Peng,
H.-X.; Zhang, L.-P.; Tung, C.-H.; Wu, L.-Z. Langmuir
2013, 29, 2843–2848; (j) Rajamalli, P.; Prasad, E. Org. Lett.
2011, 13, 3714–3717; (k) Yan, N.; Xu, Z.; Diehn, K.K.;
Raghavan, S.R.; Fang, Y.; Weiss, R.G. Langmuir 2013, 29,
793–805; (l) Varghese, R.; George, S.J.; Ajayaghosh, A.
Chem. Commun. 2005, 593–595.
Supplementary data
Experimental procedures for spectroscopic studies,
Figures showing the change in UV–vis titrations of
receptor 1 with various anions, Job plot, binding constant
curve and electrical measurement method, and character-
isation spectra of 1 can be found online.
Acknowledgements
The authors thank DST and UGC, New Delhi, India for providing
facilities in the department. DK thanks CSIR, New Delhi, India
for a fellowship.
References
(1) (a) Fages, F. Low Molecular Mass Gelators, Topics in
Current Chemistry; Springer: Berlin, 2005, Vol. 265, p 283
(b) Terech, P.; Weiss, R.G. Chem. Rev. 1997, 97, 3133–
3160; (c) Weiss, R.G.; Terech, P. Molecular Gels; Springer:
Dordrecht, 2006, p 978; (g) Nonappa; Maitra, U. Org.
Biomol. Chem. 2008, 6, 657–669; (h) Lee, K.Y.; Mooney,
D.J. Chem. Rev. 2001, 101, 1869–1880
(2) (a) Banacucina, G.; Cespi, M.; Misici-Falzi, M.; Palmieri,
G.F. J. Pharm. Sci. 2009, 98, 1–42; (b) Friggeri, A.;
Feringa, B.L.; van Esch, J. J. Controlled Release. 2004, 97,
241–248; (c) van Bommel, K.J.C.; Stuart, M.C.A.; Feringa,
B.L.; Van Esch, J. Org. Biomol. Chem. 2005, 3, 2917–2920.
(3) Miyata, T.; Uragami, T.; Nakamae, K. Adv. Drug Deliv.
Rev. 2002, 54, 79–98.
(4) (a) Esser-Kahn, A.P.; Iavarone, A.T.; Francis, M.B. J. Am.
Chem. Soc. 2008, 130, 15820–15822; (b) Dave, N.; Chan,
M.Y.; Huang, P.-J.J.; Smith, B.D.; Liu, J. J. Am. Chem. Soc.
2010, 132, 12668–12673.
(5) (a) Chen, Q.; Lv, Y.; Zhang, D.; Zhang, G.; Liu, C.; Zhu, D.
Langmuir 2010, 26, 3165–3168; (b) Pal, A.; Shrivastava,
(10) (a) Ghosh, K.; Kar, D. Org. Biomol. Chem. 2012, 10, 8800–
8807; (b) Park, M.; Jang, D.; Kim, S.Y.; Hong, J.-I. New
J. Chem. 2012, 36, 1145–1148; (c) J. Krishnamurthi, T.
Ono, S. Amemori, H. Komatsu, S. Shinkai and K. Sada,
Chem. Commun. 2011, 47, 1571–1573; (d) J. Zhou and
H. Li, Appl. Mater. Interfaces 2012, 4, 721–724; (e) J.-W.
Liu, Y. Yang, C.-F. Chen and J.-T. Ma, Langmuir 2010, 26,
9040–9044.