Authors:
Tea Mihelj Department of Physical Chemistry, Ruđer Bošković Institute, POB 180, 10002, Zagreb, Croatia

Search for other papers by Tea Mihelj in
Current site
Google Scholar
PubMed
Close
,
Zoran Štefanić Department of Physical Chemistry, Ruđer Bošković Institute, POB 180, 10002, Zagreb, Croatia

Search for other papers by Zoran Štefanić in
Current site
Google Scholar
PubMed
Close
, and
Vlasta Tomašić Department of Physical Chemistry, Ruđer Bošković Institute, POB 180, 10002, Zagreb, Croatia

Search for other papers by Vlasta Tomašić in
Current site
Google Scholar
PubMed
Close
Restricted access

Abstract

The novel surfactant–picrate compounds were synthesized and characterized by thermal and XRD analysis. The synthesis, based on the electrostatic interactions of components in polar solvents, was carried out using picric acid and cationic surfactants (dodecyltrimethylammonium, didodecyldimethylammonium, and tridodecylmethylammonium halide). The idea was to investigate the dependence of physico-chemical properties and thermal transitions of picrate–surfactant compounds with raising number of dodecyl chains sited on the same ammoniumm head group. The equimolar mixed aqueous solutions are characterized as lyotropic, strongly promoted by picrate anion. The main crystal structure feature of investigated picrates is layered structure with stacked aromatic rings of one picrate molecule on the top of the other one via strong π…π interactions and connection to the alkylammonium molecules with their nitro groups by C–H…O hydrogen bonds. Surfactant–picrate bilayer-like structures are interrupted with layers of polar heads and picrate counterions and the observed width of such a bilayers are functions of more complex structural behaviors which ensures alternation in space of equal numbers of positive and negative charges. Although some of the surfactants used posses thermotropic porperties, like examined tridodecylmethylammonium chloride, no thermotropic mesomorphism is detected in solid state of investigated surfactant–picrate compounds. The thermodynamic parameters of solid–liquid thermal transitions depend linear on the number of dodecyl chains, and for double- and triple-tailed picrate compounds the marked temporal hysteresis of the melt crystallization is registered.

  • 1. Olsher, U, Feinberg, H, Frollow, F, Shoham, G 1996 The picrate anion as a versatile chelating counter-ion for the complexation of alkali and alkaline earth metal cations with ionophores: “The picrate effect”. Pure Appl Chem 68:11951199 .

    • Crossref
    • Search Google Scholar
    • Export Citation
  • 2. Farrell, PG, Shahidi, F, Casellato, F, Vecchi, C, Girelli, A 1979 DSC studies of aromatic hydrocarbon picrates. Thermochim Acta 33:275280 .

    • Crossref
    • Search Google Scholar
    • Export Citation
  • 3. Tomašić, V, Tušek-Božić, LJ, Višnjevac, A, Kojić-Prodić, B, Filipović-Vinceković, N 2000 Physicochemical properties of dodecylammonium picrate. J Colloid Interface Sci 227:427436 .

    • Crossref
    • Search Google Scholar
    • Export Citation
  • 4. Ohba, S, Ito, Y 2002 2-(4-Hydroxyphenyl)ethylammonium picrate. Acta Cryst E 58:584585 .

  • 5. Martin Britto Dhas, SA, Natarajan, S 2008 Growth and characterization of a new potential second harmonic generation material from the amino acid family: l-Valinium picrate. Cryst Res Technol 43:869873 .

    • Crossref
    • Search Google Scholar
    • Export Citation
  • 6. Goto, M, Kanno, H, Sugaya, E, Osa, Y, Takayanagi, H 2004 Crystal structure of adenosinium picrate. Anal Sci 20:3940.

  • 7. Anitha, K, Athimoolam, S, Natarajan, S 2006 Pyridoxinium picrate. Acta Cryst C 62:426428 .

  • 8. Marchand, AP, Hazlewood, A, Huang, Z, Vadlakonda, SK, Rocha, JDR, Power, TD et al. 2003 Stabilization of a K+-(bis cage annulated 20-crown-6) complex by bidentate picrate. Struct Chem 14:279288 .

    • Crossref
    • Search Google Scholar
    • Export Citation
  • 9. Nagarajan, R 2002 Molecular packing parameter and surfactant self-assembly: the neglected role of the surfactant tail. Langmuir 18:3138 .

  • 10. Ungar, G, Tomašić, V, Xie, F, Zeng, X-b 2009 Structure of liquid crystalline aerosol-OT and its alkylammonium salts. Langmuir 25:1106711072 .

  • 11. Terreros, A, Galera-Gomez, PA, Lopez-Cabaracos, E 2000 DSC and X-ray diffraction study of polymorphism in n-alkylammonium chlorides. J Therm Anal Calorim 61:341350 .

    • Crossref
    • Search Google Scholar
    • Export Citation
  • 12. Esson, JM, Ramamurthy, N, Meyerhoff, ME 2000 Polyelectrolyte-surfactant complexes: an aqueous titration method to model ion-pairing within polymeric membranes of polyion-sensitive electrodes. Anal Chim Acta 404:8394 .

    • Crossref
    • Search Google Scholar
    • Export Citation
  • 13. Ono, Y, Kawasaki, H, Annaka, M, Maeda, H 2005 Effects of micelle-to-vesicle transitions on the degree of counterion binding. J Colloid Interface Sci 287:685693 .

    • Crossref
    • Search Google Scholar
    • Export Citation
  • 14. Marques, EF, Regev, O, Khan, A, da Graca Miguel, M, Lindman, B 1999 Vesicle formation and general phase behavior in the catanionic mixture SDS–DDAB–water. The cationicrich side. J Phys Chem B 103:83538363 .

    • Crossref
    • Search Google Scholar
    • Export Citation
  • 15. Harms, K, Wolcado, S 1995 XCAD4-CAD4 data reduction Universitiy of Marburg Germany.

  • 16. Farrugia, LJ, Win, GX 1999 Suite for single crystal small molecule crystallography. J Appl Cryst 32:837838 .

  • 17. Sheldrick, GM 1997 SHELX97: program for the refinement of the crystal structures Universitiy of Gottingen Germany.

  • 18. Spek, AL 2001 PLATON 98: a multipurpose crystallographic tool 101201 version University of Utrecht Utrecht, The Netherlands.

  • 19. Macrae, CF, Edgington, PR, McCabe, P, Pidcock, E, Shields, GP, Taylor, R et al. 2006 Mercury: visualization and analysis of crystal structures. J Appl Cryst 39:453457 .

    • Crossref
    • Search Google Scholar
    • Export Citation
  • 20. Finch, A, Smith, AE 1982 Thermochemistry of picrates. III. Enthalpies of solution and solubities of picrate salts. Thermochim Acta 53:349356 .

    • Crossref
    • Search Google Scholar
    • Export Citation
  • 21. Everaert, J, Persoons, A 1981 Dissociation mechanism of tetrabutylammonium picrate ion pairs in media of low polarity. 1. A sphere-in-continuum approach. J Phys Chem 85:39303937 .

    • Crossref
    • Search Google Scholar
    • Export Citation
  • 22. Khan, MA 1986 Hydrogen bonding and crystal packing trends in tetraalkylammonium halide-catechol complexes: synthesis, spectroscopic and crystal structure studies of Me4NC1-catechol, Et4NCl-catechol, Et4NBr-catechol and Pr4NBr-catechol complexes. J Mol Struct 145:203218 .

    • Crossref
    • Search Google Scholar
    • Export Citation
  • 23. Rupert, LAM, Hoekstra, D, Engberts, JBFN 1985 Fusogenic behavior of didodecyldimethylammonium bromide bilayer vesicles. J Am Chem Soc 107:26282631 .

    • Crossref
    • Search Google Scholar
    • Export Citation
  • 24. Kamitori, S, Sumimoto, V, Vongbupnimit, K, Noguchi, K, Okuyama, K 1997 Molecular and crystal-structures of dodecyltrimethylammonium bromide and its complex with P-Phenylphenol. Mol Cryst Liq Cryst 300:3143 .

    • Crossref
    • Search Google Scholar
    • Export Citation
  • 25. Okuyana, K, Soboi, Y, Ijima, N, Hirabayashi, K, Kunitake, T, Kajiyama, T 1988 Molecular and crystal structure of the lipid-model amphiphile, dioctadecyldimethylammonium bromide monohydrate. Bull Chem Soc Jpn 61:14851490 .

    • Crossref
    • Search Google Scholar
    • Export Citation
  • 26. Alami, E, Levy, H, Zana, R, Weber, P, Skoulios, A 1993 A new smectic mesophase with two dimensional tetragonal symmetry from dialkyldimethylammonium bromides: ST. Liq Cryst 13:201212 .

    • Crossref
    • Search Google Scholar
    • Export Citation
  • 27. Iwamoto, K, Ohnuki, Y, Sawada, K, Senō, M 1981 Solid-solid phase transitions of long-chain n-alkyltrimethylammonium halides. Mol Cryst Liq Cryst 73:95103 .

    • Crossref
    • Search Google Scholar
    • Export Citation
  • 28. Malliaris, A, Christias, C, Margomenou-Leonidopoulou, G, Paleos, CM 1982 Single chain quaternary ammonium salts exhibiting thermotropic mesomorphism and organization in water. Mol Cryst Liq Cryst 82:161166 .

    • Crossref
    • Search Google Scholar
    • Export Citation
  • 29. Gilson, DFR, Kertes, AS, Manley, RSJ, Tsau, J, Donnay, G 1976 Polymorphism in n-alkylammonium chlorides: X-ray powder diffraction studies. Can J Chem 54:765768 .

    • Crossref
    • Search Google Scholar
    • Export Citation
  • Collapse
  • Expand

To see the editorial board, please visit the website of Springer Nature.

Manuscript Submission: HERE

For subscription options, please visit the website of Springer Nature.

Journal of Thermal Analysis and Calorimetry
Language English
Size A4
Year of
Foundation
1969
Volumes
per Year
1
Issues
per Year
24
Founder Akadémiai Kiadó
Founder's
Address
H-1117 Budapest, Hungary 1516 Budapest, PO Box 245.
Publisher Akadémiai Kiadó
Springer Nature Switzerland AG
Publisher's
Address
H-1117 Budapest, Hungary 1516 Budapest, PO Box 245.
CH-6330 Cham, Switzerland Gewerbestrasse 11.
Responsible
Publisher
Chief Executive Officer, Akadémiai Kiadó
ISSN 1388-6150 (Print)
ISSN 1588-2926 (Online)

Monthly Content Usage

Abstract Views Full Text Views PDF Downloads
Mar 2024 44 2 0
Apr 2024 10 0 0
May 2024 3 0 0
Jun 2024 5 0 0
Jul 2024 36 0 0
Aug 2024 26 0 0
Sep 2024 4 0 0