Supramolecular Chemistry Research Unit (SCRU)

Synthesis of the derivatives of calix[4]arene and related macrocyclic compounds that possess suitable cavity and donor sets for complexing anions, transition metal ions and organic molecules.

Uses of synthesized compounds for applications in sensors and as supramolecular devices.

• 1998 Thailand Young Scientist Award (awarded by the Foundation for the Promotion of Science and Technology under the Patronage of His Majesty the King)
• 1998 The Professor Fund Award (awarded by the Faculty of Science, Chulalongkorn University)
• 2001 Finalist in ASEAN Young Scientist and Technologist Award
• 2002 Science and Technology Awards (awarded by the Thailand Toray Science Foundation)
• 2005 Most cited author award (awarded by the Faculty of Science, Chulalongkorn University)

Publications:

1. Kaewwangchai, S.; Tuntulani, T.; Ruangpornvisuti, V. "Molecular Structure of 3,6-Di(hexylthioureido)acridine Conformers, Their Protonation, 1H NMR and IR Analyses: Theoretical and Experimental Studies" J. Mol. Struc. 2007, in press.
2. Ngeontae, W.; Aeungmaitrepirom, W.; Tuntulani, T. "Chemically modified silica gel with aminothioamidoanthraquinone for solid phase extraction and preconcentration of Pb(II), Cu(II), Ni(II), Co(II) and Cd(II)" Talanta 2007, 71, 1075-1082.
3. Suksai, C.; G?mez, S. F.; Chhabra, A.; Liu, J: Skepper, J. N.; Tuntulani, T.; Otto, S. "Guest-Induced Morphological Transformations of Aggregates of an Amphiphilic Receptor" Langmuir 2006, 22, 5994-5997.
4. Morakot, N.; Tomapatanaget, B.; Aeungmaitripirom, W.; Ngeon-tae, V. "Synthesis and Fluorescence Sensing Properties of Calix[4]arenes Containing Fluorophores" Supramol. Chem. 2005, 17, 655-659.
5. Rojanathanes, R.; Tuntulani, T.; Bhanthumnavin, W.; Sukwattanasinitt, M. "Stilbene-Bridged tert-Butylcalix[4]arene as Photoswitchable Molecular Receptors" Org. Lett. 2005, 7, 3401-3404.
6. Kerdpaiboon, N.; Tomapatanaget, B.; Chailapakul, O.; Tuntulani, T. "Calix[4]quinones Derived from Double Calix[4]arenes: Synthesis, Complexation and Electrochemical Properties towards Alkali Metal Ions" J. Org. Chem. 2005, 70, 4797-4804.
7. Harding, D. J.; Adams, H.; Tuntulani, T. "B-N Bond Cleavage by Cobalt(II) in Acetato(3,5-diphenylpyrazole)[tris(3,5-diphenylpyrazolyl)borato]Cobalt(II)" Acta Cryst. 2005, C61, m301-m303.
8. Suksai, C.; Tuntulani, T. "Chromogenic Anion Sensors" Top. Curr. Chem. 2005, 255, 163-198.
9. Suksai, C.; Leeladee, P.; Jainuknan, D.; Tuntulani, T.; Muangsin, N.; Chailapakul, O.; Kongsaeree, P.; Pakavatchai, C. "A New Heteroditopic Receptor and Sensor Highly Selective for Bromide in the Presence of A Bound Cation" Tetrahedron Lett. 2005, 46, 2765-2769.
10. Rojanathanes, R.; Pipoosananakaton, B.; Tuntulani, T.; Bhanthumnavin, W.; Orton, J. B.; Cole, S. J.; Hursthouse, M. B.; Grossel, M. C.; Sukwattanasinitt, M. "Comparative Study of Azobenzene and Stilbene Bridged Crown Ether p-tert-Butylcalix[4]arene" Tetrahedron 2005, 61, 1317-1324.
11. Tomapatanaget, B.; Tuntulani, T.; Wisner, J. A.; Beer, P. D. "New Interlocked Molecules Generating from a Podand Containing Urea Units and Imidazolium Salts Using an Anion Template" Tetrahedron Lett. 2004, 45, 663-666.
12. Tumcharern, G.; Tuntulani, T.; Coles, S. J.; Hursthouse, M. B.; Kilburn, J. D. "A Novel Ditopic Receptor and Reversal of Anion Binding Selectivity in the Presence and Absence of Bound Cation" Org. Lett. 2003, 5, 4971-4974.
13. Sukwattanasinitt, M.; Nantalaksakul, A.; Potisatityuenyong, A.; Tuntulani, T.; Chailapakul, O.; Prapairaksit, N. "An Electrochemical Sensor from a Soluble Polymeric Ni-salen Complex" Chem. Mater. 2003, 15, 4337-4339.
14. Wanno, B.; Sang-aroon, W.; Tuntulani T.; Polpoka, B.; Ruangpornvitsuti, V. "Conformational and energetical structures of sulfonylcalix[4]arene, p-tert-butylsulfonylcalix[4]arene and their zinc complexes" J. Mol. Struc.-Theochem. 2003, 629, 137-150.
15. Suksai, J.; Tuntulani, T. "Chromogenic Anion Sensors" Chem. Soc. Rev. 2003, 32, 192-202.
16. Tomapatanaget, B.; Tuntulani, T.; Chailapakul, O. "Calix[4]arenes Containing Ferrocene Amide as Carboxylate Anion Receptors and Sensors" Org. Lett. 2003, 5, 1539-1542.
17. Tantrakarn, K.; Ratanatawanate, C.; Pinsuk, T.; Chailapakul, O.; Tuntulani, T. "Synthesis of Redox-Active Biscalix[4]quinones and Their Electrochemical Properties" Tetrahedron Lett. 2003, 44, 33-36.
18. Tongraung, P; Chantarasiri, N.; Tuntulani, T. "Calix[4]arenes Containing Urea and Crown/Urea Moieties: Effects of the Crown Ether Unit and Na+ towards Anion Binding Ability" Tetrahedron Lett. 2003, 44, 29-32.
19. Tuntulani, T.; Thavornyutikarn, P.; Poompradub, S.; Jaiboon, N.; Ruangpornvisuti, V.; Chaichit, N.; Asfari, Z.; Vicens, J. "Synthesis of Tripodal Aza Crown Ether Calix[4]arenes and Their Supramolecular Chemistry with Transition-, Alkali Metal Ions and Anions" Tetrahedron 2002, 58, 10277-10285.
20. Tuntulani, T. "Book Review: Calixarenes 2001" J. Inclu. Phenom. 2002, 43, 149-151.
21. Ruangpornvisuiti, V.; Pulpoka, B.; Tuntulani, T.; Thipyapong, K.; Suksai, C. "Conformational Investigations of HMPAO Isomers and Their Zinc(II) Complexes" Bull. Kor. Chem. Soc. 2002, 23, 555-562.
22. Sukwattanasinitt, M.; Rojanathanes, R.; Tuntulani, T.; Ruangpornvisuti, V. "Selective Oxidation of 25,27-Di-(3'-formylphenoxyethoxy)-p-tert-butylcalix[4]arene" ScienceAsia 2002, 28, 25-28.
23. Tomapatanaget, B.; Tuntulani, T. "Lower Rim Tetra-Substituted and Upper Rim Ferrocene Amide Calix[4]Arenes: Synthesis, Conformation and Anion Binding Properties" Tetrahedron Lett. 2001, 42, 8105-8109.
24. Tuntulani, T.; Poompradub, S.; Thavornyutikarn, P.; Jaiboon, N.; Ruangpornvisuti, V.; Chaichit, N.; Asfari, Z.; Vicens, J. "Aza Crown Ether Calix[4]arenas Containing Cation and Anion Binding Sites: Effects of Cations towards Anion Binding Ability" Tetrahedron Lett. 2001, 42, 5541-5544.
25. Sukwattanasinitt, M.; Rojanathanes, R.; Tuntulani, T.; Sritana-Anant, Y.; Ruangpornvisuti, V. "Synthesis of Stilbene Crown Ether p-tert-Butylcalix[4]arenes" Tetrahedron Lett. 2001, 42, 5291-5293.
26. Tuntulani, T.; Tumcharern, G.; Ruangpornvisuti, V. "Recognition Studies of a Pyridine-Pendant Calix[4]arene with Neutral Molecules: Effects of Non-Covalent Interactions on Supramolecular Structures and Stabilities" J. Inclu. Phenom. 2001, 39, 47-53.
27. Jaiboon, N.; Chaichit, C.; Pipoosananakaton, B.; Tuntulani, T.; Sukwattanasinitt, M. "Crystal Structure of Diethoxynitrobenzene-p-tert-Butylcalix[4]areneo2(CH3)2C=O: Evidence of Intra- and Intermolecular CH/ Interactions Forced by Crystal Packing" J. Chem. Cryst. 2000, 30, 717-720.
28. Tuntulani, T.; Tumcharern, G.; Volkmer, D. "S- and NH- Bridging Pyridine- and Pyrimidine-Based Ligands for 2x2, 3x3 and 4x4 Molecular grids: Evidence of [2x2]Zn(II) Grids" Bull. Kor. Chem. Soc. 2000, 21, 1245-1248.
29. Pulpoka, B.; Jamkrotoke, M.; Tuntulani, T.; Ruangpornvisuti, V. "Synthesis of 1,3-Alternate Calix[4]-Cyclen-Benzo-Crown-6 as a Hard-Soft Receptor" Tetrahedron Lett. 2000, 41, 9167-9171.
30. Pipoosananakaton, B.; Sukwattanasinitt, M.; Jaiboon, N.; Chaichit, N.; Tuntulani, T. "Preparation of New Azobenzene Crown Ether p-tert-Butylcalix[4]arenes and Their Roles as Switchable Ionophores for Na+ and K+ Ions" Tetrahedron Lett. 2000, 41, 9095-9100.
31. Pipoosananakaton, B.; Sukwattanasinitt, M.; Jaiboon, N.; Chaichit, N.; Tuntulani, T. "New Azobenzene Crown p-tert-Butylcalix[4]arenes as Switchable Receptors for Na+ and K+ ions: Synthesis and Isomerization Studies" Bull. Kor. Chem. Soc. 2000, 21, 867-874.
32. Veravong, S.; Ruangpornvisuti, V.; Pipoosananakaton, B.; Sukwattanasinitt, M.; Tuntulani, T. "Synthesis of Tetraalkylated Calix[4]arenes and Studies of Their Conformational Behaviors" ScienceAsia 2000, 26, 163-170.
33. Navakun, K.; Tuntulani, T.; Ruangpornvisuti, V. "p-tert-Butylcalix[4]arene Derivatives Containing Azathiol Recepting Units and Their Recognition towards Hg(II)" J. Inclu. Phenom. 2000, 38, 113-122.
34. Chantarasiri, N.; Tuntulani, T.; Chanma, N. "Application of Hexadentate Schiff Base Metal Complexes as Crosslinking Agents for Diglycidyl Ether of Bisphenol A" Eur. Polym. J. 2000, 36, 889-894.
35. Chantarasiri, N.; Tuntulani, T.; Tongraung, P; Wannarong, W.; Seangprasertkij-Magee, R. "New Metal-Containing Epoxy Polymers from Diglycidyl Ether of Bisphenol A and Tetradentate Schiff Base Metal Complexes" Eur. Polym. J. 2000, 36, 695-702.
36. Suwattanamala, E.; Tuntulani, T.; Ruangpornvisuti, V. "Quantum Chemical Investigations on Stabilities of Protonated Species of 25,27-{2,2'-(2,2'-((2,5,8-triaza)nonyl)diphenoxy)diethyl}-p-tert-butylcalix[4]arene" ScienceAsia 1999, 25, 207-210.
37. Tomapatanaget, B.; Pulpoka, P.; Tuntulani, T. "Preparation of Diaza Dioxa Dithia Crown p-tert-Butylcalix[4]arene by S-Alkylation Reactions: Use of Metallo-Calix[4]arene Complexes as Reaction Templates" Chem. Lett. 1998, 1037-1038.
38. Grapperhaus, G. A.; Tuntulani, T.; Reibenspies, J. H.; Darensbourg, M. Y. "Methylation of Tethered Thiolates in [(bme-daco)Zn]2 and [(bme-daco)Cd]2 as a Model of Zinc Sulfur-Methylation Proteins" Inorg. Chem. 1998, 37, 4052-4058.
39. Mills, D. K.; Font, I.; Farmer, P. J.; Hsiao, Y.-M.; Tuntulani, T.; Buonomo, R. M.; Goodman, C. G.; Musie, G; Grapperhaus, C. A.; Maguire, M. J.; Lai, C.-H.; Hatley, M. L.; Smee, J. J.; Bellefeuille, J. A.; Darensbourg, M. Y. "1,5-Diazacyclooctane, Pendent Arm Thiolato Derivatives and [N,N'-Bis(2-mercaptoethyl)-1,5-diazacyclooctanato]nickel(II)" Inorg. Synth. 1998, 32, 89-98.
40. Tuntulani, T.; Volkmer, D.; Fenske, D.; Lehn, J.-M. "The Novel N-Donor Heterocyclic Ligands and Their Coordination Chemistry Towards a Cu(II) Salt" J. Sci. Soc. Thailand 1997, 23, 185-198.
41. Tuntulani, T.; Ruangpornvisuti, V.; Tantikunwatthana, N.; Ngampaiboonsombut, O.; Seangprasertkij-Magee, R.; Asfari, Z.; Vicens, J. "Synthesis of the Tripodal-Amine Capped Benzo Crown p-tert-Butylcalix[4]arene and Its Host-Guest Chemistry" Tetrahedron Letters 1997, 38, 3985-3988.
42. Pothsree, T.; Seangprasertkij-Magee, R.; Tuntulani, T. "Anion and Cavity Effects on the Complexation Behavior of Di-Aza-Benzo-Crown-Ether Calix[4]arene towards Zn(II) Ions" J. Inclu. Phenom. 1997, 29, 99-107.
43. Rojsajjakul, T.; Veravong, S.; Tumcharern, G; Seangprasertkij-Magee, R.; Tuntulani, T. "Synthesis and Characterization of Polyaza Crown Ether Derivatives of Calix[4]arene and Their Role as Anion Receptors" Tetrahedron 1997, 53, 4669-4680.
44. Grapperhaus, C. G.; Maguire, M. J.; Tuntulani, T.; Darensbourg, M. Y. "Singlet Oxygen and the Production of Sulfur Oxygenates of Nickel(II) and Palladium(II) Thiolates" Inorg. Chem. 1997, 36, 1860-1866.
45. Musie, G.; Farmer, P. J.; Tuntulani, T.; Reibenspies, J. H.; Darensbourg, M. Y. "Influence of Sulfur Metalation on the Accessibility of the NiII/I Couple in [N,N'-Bis (2-mercaptoethyl)-1,5-diazacyclooctanato]nickel(II): Insight into the Redox Properties of [NiFe]-Hydrogenase" Inorg. Chem. 1996, 35, 2176-2183.
46. Darensbourg, M. Y.; Tuntulani, T.; Reibenspies, J. H. "Structure/Function Relationships in Ligand-Based SO2/O2 Conversion to Sulfate As Promoted by Nickel and Palladium Thiolates" Inorg. Chem. 1995, 34, 6287-6294.
47. Tuntulani, T.; Musie, G.; Darensbourg, M. Y.; Reibenspies, J. H. "Metallosulfoxides and -sulfones: Sufur Oxygenates of [1,5-Bis(2-mercaptoethyl)-1,5-diazacyclooctanato] palladium(II)" Inorg. Chem. 1995, 34, 6279-6286.
48. Buonomo, R. M.; Font, I.; Maguire, M. J.; Reibenspies, J. H.; Tuntulani, T.; Darensbourg, M. Y. "Study of Sulfinate and Sulfenate Complexes Derived from the Oxygenation of Thiolate Sulfur in [1,5-Bis(2-mercapto-2-methlpropyl)-1,5-diazacyclo-octanato(2-)]nickel(II)"J. Am. Chem. Soc. 1995, 117, 963-973.
49. Darensbourg, M. Y.; Tuntulani, T.; Reibenspies, J. H. "Sulfur Site Adducts of Sulfur Dioxide in Nickel-Bound Thiolates and Their Conversion to Sulfate" Inorg. Chem. 1994,33, 611-613.
50. Goodman, D. C.; Tuntulani, T.; Reibenspies, J. H.; Farmer, P. J.; Darensbourg, M. Y. "Axial Ligation of Diazacyclooctanenickel and -Zinc Complexes" Angew. Chem. Int. Ed. Engl. 1993, 32, 116-119.
51. Tuntulani, T; Reibenspies, J. H.; Farmer, P. J.; Darensbourg, M. Y. "Preparations and Structures of a Zinc(II) Dimer and Zinc(II)/Nickel(II) Pentanuclear Derivatives of N,N'-bis(mercaptoethyl)-1,5-diazacyclooctane: [(BME-DACO)Zn]2 and {[(BME-DACO)Ni]3[ZnCl]2}{BF4}2" Inorg.Chem. 1992, 31, 3497-3499.