Skip to main content
SpringerLink
Log in

Efficient Encapsulation of Chloroform with Cryptophane-M and the Formation of Exciplex Studied by Fluorescence Spectroscopy

  • Original Paper
  • Published:
Journal of Fluorescence Aims and scope Submit manuscript

Abstract

Efficient encapsulation of small molecules with supermolecules is one of significantly important subjects due to strong application potentials. This article presents the interaction between cryptophane-M and chloroform by fluorescence spectroscopy. The sonicated cryptophane-M solution exhibits light green color in chloroform, and the solid obtained from the evaporation of chloroform also has different color from that of cryptophane-M. In contrast, the sonicated cryptophane-M solutions in other solvents are colorless, and the solid obtained from the evaporation of these solvents has the same color as that of cryptophane-M. Furthermore, the freshly prepared cryptophane-M solution in different solvents is almost colorless, and the solid obtained from the evaporation of these solvents displays the same color as that of cryptophane-M. Although the sonicated cryptophane-M solutions in different solvents have very similar absorption spectra, they exhibit quite different emission spectra in chloroform. In contrast, the freshly-prepared cryptophane-M solutions show similar absorption and emission spectroscopy in various solvents. The variation of the fluorescence spectroscopy in binary solvents with the increasing chloroform ratio suggests that cryptophane-M and chloroform form a 1:1 exciplex, and the binding constant is estimated to be 292.95 M−1. Although all solvents are able to enter into the cavity of cryptophane-M, only chloroform can stay in the cavity of cryptophane-M for a while, which is mostly due to the strong intermolecular interaction between cryptophane-M and chloroform, and this results in the formation of the exciplex between them.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Scheme 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Fig. 8
Fig. 9

Similar content being viewed by others

References

  1. Brotin T, Dutasta JP (2009) Cryptophanes and their complexes#present and future. Chem Rev 109(1):88–130

    Article  PubMed  CAS  Google Scholar 

  2. Chaffee KE, Fogarty HA, Brotin T, Goodson BM, Dutasta JP (2009) Encapsulation of small gas molecules by cryptophane-111 in organic solution. 1. Size- and shape-selective complexation of simple hydrocarbons. J Phys Chem A 113(49):13675–13684

    Article  PubMed  CAS  Google Scholar 

  3. Diez NM, de la Pena AM, Garcia MCM, Gil DB, Canada-Canada F (2007) Fluorimetric determination of sulphaguanidine and sulphamethoxazole by host-guest complexation in beta-cyclodextrin and partial least squares calibration. J Fluoresc 17(3):309–318

    Article  PubMed  CAS  Google Scholar 

  4. Enoch IVMV, Swaminathan M (2006) Fluorimetric study on molecular recognition of beta-cyclodextrin with 2-amino-9-fluorenone. J Fluoresc 16(4):501–510

    Article  PubMed  CAS  Google Scholar 

  5. Chen Y, Pang Y, Wu JL, Su Y, Liu JY, Wang RB, Zhu BS, Yao YF, Yan DY, Zhu XY, Chen Q (2010) Controlling the Particle Size of Interpolymer Complexes through Host-Guest Interaction for Drug Delivery. Langmuir 26(11):9011–9016

    Article  PubMed  CAS  Google Scholar 

  6. Benounis M, Jaffrezic-Renault N, Dutasta JP, Cherif K, Abdelghani A (2005) Study of a new evanescent wave optical fibre sensor for methane detection based on cryptophane molecules. Sens Actuators B 107(1):32–39

    Article  Google Scholar 

  7. Kim BS, Ko YH, Kim Y, Lee HJ, Selvapalam N, Lee HC, Kim K (2008) Water soluble cucurbit[6]uril derivative as a potential Xe carrier for Xe-129 NMR-based biosensors. Chem Commun 24:2756–2758

    Article  Google Scholar 

  8. Marjanska M, Goodson BM, Castiglione F, Pines A (2003) Inclusion complexes oriented in thermotropic liquid-crystalline solvents studied with carbon-13 NMR. J Phys Chem B 107(46):12558–12561

    Article  CAS  Google Scholar 

  9. Chaffee KE, Marjanska M, Goodson BM (2006) NMR studies of chloroform@cryptophane-A and chloroform@bis-cryptophane inclusion complexes oriented in thermotropic liquid crystals. Solid State Nucl Mag 29(1–3):104–112

    Article  CAS  Google Scholar 

  10. Bouchet A, Brotin T, Cavagnat D, Buffeteau T (2010) Induced chiroptical changes of a water-soluble cryptophane by encapsulation of guest molecules and counterion effects. Chem Eur J 16(15):4507–4518

    Article  CAS  Google Scholar 

  11. Martinez A, Robert V, Gornitzka H, Dutasta JP (2010) Controlling helical chirality in atrane structures: solvent-dependent chirality sense in hemicryptophane-oxidovanadium(V) complexes. Chem Eur J 16(2):520–527

    Article  CAS  Google Scholar 

  12. Tosner Z, Lang J, Sandstrom D, Petrov O, Kowalewski J (2002) Dynamics of an inclusion complex of dichloromethane and cryptophane-E. J Phys Chem A 106(38):8870–8875

    Article  CAS  Google Scholar 

  13. Lang J, Dechter JJ, Effemey M, Kowalewski J (2001) Dynamics of an inclusion complex of chloroform and cryptophane-E: Evidence for a strongly anisotropic van der Waals bond. J Am Chem Soc 123(32):7852–7858

    Article  PubMed  CAS  Google Scholar 

  14. Roesky CEO, Weber E, Rambusch T, Stephan H, Gloe K, Czugler M (2003) A new cryptophane receptor featuring three endo-carboxylic acid groups: Synthesis, host behavior and structural study. Chem Eur J 9(5):1104–1112

    Article  CAS  Google Scholar 

  15. Tosner Z, Petrov O, Dvinskikh SV, Kowalewski J, Sandstrom D (2004) A C-13 solid-state NMR study of cryptophane-E: chloromethane inclusion complexes. Chem Phys Lett 388(1–3):208–211

    Article  CAS  Google Scholar 

  16. Garcia C, Humiliere D, Riva N, Collet A, Dutasta JP (2003) Kinetic and thermodynamic consequences of the substitution of SMe for OMe substituents of cryptophane hosts on the binding of neutral and cationic guests. Org Biomol Chem 1(12):2207–2216

    Article  PubMed  CAS  Google Scholar 

  17. Brotin T, Cavagnat D, Dutasta JP, Buffeteau T (2006) Vibrational circular dichroism study of optically pure cryptophane-A. J Am Chem Soc 128(16):5533–5540

    Article  PubMed  CAS  Google Scholar 

  18. Sun P, Jiang YD, Xie GZ, Du XS, Hu J (2009) A room temperature supramolecular-based quartz crystal microbalance (QCM) methane gas sensor. Sens Actuators B 141(1):104–108

    Article  Google Scholar 

  19. Crassous J, Collet A (2000) The bromochlorofluoromethane saga. Enantiomer 5(5):429–438

    PubMed  CAS  Google Scholar 

  20. Garel L, Lozach B, Dutasta JP, Collet A (1993) Remarkable effect of receptor size in the binding of acetylcholine and related ammonium-ions to water-soluble cryptophanes. J Am Chem Soc 115(24):11652–11653

    Article  CAS  Google Scholar 

  21. Taratula O, Dmochowski IJ (2010) Functionalized 129Xe contrast agents for magnetic resonance imaging. Curr Opin Chem Biol 14(1):97–104

    Article  PubMed  CAS  Google Scholar 

  22. Brotin T, Darzac M, Forest D, Becchi M, Dutasta JP (2001) Formation of cryptophanes from their precursors as viewed by liquid secondary ion mass spectrometry. J Mass Spectrom 36(10):1092–1097

    Article  PubMed  CAS  Google Scholar 

  23. Huber G, Beguin L, Desvaux H, Brotin T, Fogarty HA, Dutasta JP, Berthault P (2008) Cryptophane-xenon complexes in organic solvents observed through NMR spectroscopy. J Phys Chem A 112(45):11363–11372

    Article  PubMed  CAS  Google Scholar 

  24. Petrov O, Tosner Z, Csoregh I, Kowalewski J, Sandstrom D (2005) Dynamics of chloromethanes in cryptophane-E inclusion complexes: A H-2 solid-state NMR and X-ray diffraction study. J Phys Chem A 109(20):4442–4451

    Article  PubMed  CAS  Google Scholar 

  25. Cavagnat D, Brotin T, Bruneel JL, Dutasta JP, Thozet A, Perrin M, Guillaume F (2004) Raman microspectrometry as a new approach to the investigation of molecular recognition in solids: Chloroform-cryptophane complexes. J Phys Chem B 108(18):5572–5581

    Article  CAS  Google Scholar 

  26. Zhang CH, Shen WL, Wen GM, Chao JB, Qin LP, Shuang SM, Dong C, Choi MMF (2008) Spectral study on the interaction of cryptophane-A and neutral molecules CHnCl4-n (n=0, 1, 2). Talanta 76(2):235–240

    Article  PubMed  CAS  Google Scholar 

  27. Zhang CH, Shen WL, Fan RY, Zhang GM, Shuang SM, Dong C, Choi MMF (2010) Spectral study on the inclusion complex of cryptophane-E and CHCl3. Spectrochim, Acta Part A 75(1):157–161

    Article  Google Scholar 

  28. Perrin DD, Armarego WLF, Perrin DR (1966) Purification of Laboratory Chemicals. Pergamon, New York

    Google Scholar 

  29. Canceill J, Collet A (1988) Two-step synthesis of D3 and C3h cryptophanes. JCS Chem Comm 9:582–584

    Article  Google Scholar 

  30. Eaton DF (1988) Reference materials for fluorescence measurement. Pure & Appl Chem 60(7):1107–1114

    Article  CAS  Google Scholar 

  31. Maus M, Retigg W, Bonafoux D, Lapouyade R (1999) Photoinduced intramolecular charge transfer in a series of differently twisted donor-acceptor biphenyls as revealed by fluorescence. J Phys Chem A 103(18):3388–3401

    Article  CAS  Google Scholar 

  32. Lukeman M, Veal D, Wan P, Ranjit V, Munasinghe N, Corrie JET (2004) Photogeneration of 1, 5-naphthoquinone methides via excited-state (formal) intramolecular proton transfer (ESIPT) and photodehydration of 1-naphthol derivatives in aqueous solution. Can J Chem 82:240–253

    Article  CAS  Google Scholar 

  33. The supporting data are available electronically on the supplementary material at http://www.springerlink.com/content/104905/

  34. Kandagal PB, Ashoka S, Seetharamappa J, Shaikh SMT, Jadegoud Y, Ijare OB (2006) Study of the interaction of an anticancer drug with human and bovine serum albumin: spectroscopic approach. J Pharm Biomed Anal 41(2):393–399

    Article  PubMed  CAS  Google Scholar 

  35. Hyperchem 8.0 Package, Hyperchem Inc., Gainesville, FL

Download references

Acknowledgements

The work was supported by the National Natural Science Foundation of China (No.60871039), the Science and Technology Development Project of Chongqing (No.2009AC6157) and the Fundamental Research Funds for the Central Universities (No.CDJXS10122217).

Author information

Authors and Affiliations

  1. College of Chemistry and Chemical Engineering, Chongqing University, Chongqing, 400044, China

    Yanqi Shi, Xueming Li & Fang Gao

  2. Key Laboratory for Optoelectronic Technology & Systems of the Ministry of Education, College of Optoelectronic Engineering, Chongqing University, Chongqing, 400044, China

    Jianchun Yang & Chuanyi Tao

Authors
  1. Yanqi Shi
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Xueming Li
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Jianchun Yang
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Fang Gao
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Chuanyi Tao
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Xueming Li.

Electronic Supplementary Material

Below is the link to the electronic supplementary material.

ESM 1

(DOC 261 kb)

Rights and permissions

Reprints and permissions

About this article

Cite this article

Shi, Y., Li, X., Yang, J. et al. Efficient Encapsulation of Chloroform with Cryptophane-M and the Formation of Exciplex Studied by Fluorescence Spectroscopy. J Fluoresc 21, 531–538 (2011). https://doi.org/10.1007/s10895-010-0739-5

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10895-010-0739-5

Keywords

Search

Navigation