The effect of alkali and ce(III) ions on the response properties of benzoxazine supramolecules prepared via molecular assembly

Molecules

Volumn 17, Issue 1, 2012, Pages 511-526

  Kaewvilai, Attaphon ^a   Rujitanapanich, Sawittree ^b   Wattanathana, Worawat ^a   Veranitisagul, Chatchai ^c   Suramitr, Songwut ^a   Koonsaeng, Nattamon ^a   Laobuthee, Apirat ^a  

^a KASETSART UNIVERSITY   (Thailand)

^b Phranakhon Rajabhat University   (Thailand)

^c RAJAMANGALA UNIVERSITY OF TECHNOLOGY THANYABURI   (Thailand)

Author keywords

Benzoxazine monomers; Complexation; Molecular assembly; Pedersen's technique; Supramolecules

Indexed keywords

3,4 DIHYDRO 3 (2' HYDROXYETHYLENE) 6 ETHYL 2H BENZOXAZINE; 3,4 DIHYDRO 3 (2' HYDROXYETHYLENE) 6 METHOXY 2H BENZOXAZINE; 3,4 DIHYDRO 3 (2' HYDROXYETHYLENE) 6 METHYL 2H BENZOXAZINE; 3,4-DIHYDRO-3-(2'-HYDROXYETHYLENE)-6-ETHYL-2H-BENZOXAZINE; 3,4-DIHYDRO-3-(2'-HYDROXYETHYLENE)-6-METHOXY-2H-BENZOXAZINE; 3,4-DIHYDRO-3-(2'-HYDROXYETHYLENE)-6-METHYL-2H-BENZOXAZINE; ALKALI METAL; BENZOXAZINE DERIVATIVE; CERIUM; COORDINATION COMPOUND; NANOPARTICLE;

ARTICLE; CHEMICAL MODEL; CHEMISTRY; COMPUTER SIMULATION; INFRARED SPECTROSCOPY; ISOLATION AND PURIFICATION; PARTICLE SIZE; POWDER DIFFRACTION; SYNTHESIS; THERMODYNAMICS; X RAY DIFFRACTION;

BENZOXAZINES; CERIUM; COMPUTER SIMULATION; COORDINATION COMPLEXES; METALS, ALKALI; MODELS, CHEMICAL; NANOPARTICLES; PARTICLE SIZE; POWDER DIFFRACTION; SPECTROSCOPY, FOURIER TRANSFORM INFRARED; THERMODYNAMICS; X-RAY DIFFRACTION;

EID: 84856156018     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules17010511     Document Type: Article

References (25)

1. Steed, J.W.; Atwood, J.L. Supramolecular Chemistry; John Wiley & Sons, Ltd.: Chichester, UK, 2000; p. 116.
2. Arduni, A.; Pochini, A.; Reverberi, S.; Ungaro, R. The preparation and properties of a new lipophilic sodium selective ether ester ligand derived from p-t-butylcalix[4]arene. Tetrahedron 1986, 42, 2089-2100.
3. Böhmer, V. Calixarenes, macrocycles with (almost) unlimited possibilities. Angrew. Chem. Int. Ed. Engl. 1995, 34, 713-745.
4. Sone, T.; Ohba, Y.; Yamazaki, H. Inclusion Properties of Acyclic p-Substituted Phenol- Formaldehyde Oligomers. Bull. Chem. Soc. Jpn. 1989, 62, 1111.
5. Yamagishi, T.; Tani, K.; Ishida, S.; Nakamoto, Y. Linear all-ortho oligomers of phenolformaldehyde resins. Polym. Bull. 1994, 33, 281.
6. Chirachanchai, S.; Laobuthee, A.; Phongtamrug, S.; Siripattanasarakit, W.; Ishida, H. A novel ion extraction material using host-guest properties of oligobenzoxazine local structure and benzoxazine monomer molecular assembly. J. Appl. Polym. Sci. 2000, 77, 2561.
7. Laobuthee, A.; Chirachanchai, S.; Ishida, H.; Tashiro, K. Asymmetric Mono-oxazine: An Inevitable Product from Mannich Reaction of Benzoxazine Dimers. J. Am. Chem. Soc. 2001, 123, 9947.
8. Laobuthee, A.; Chirachanchai, S. A simple, effective, and selective synthesis route for difunctional 30-membered macrocyclic ester and linear oligoester derived from benzoxazine dimers. Chem. Lett. 2002, 6, 613-614.
9. Chirachanchai, S.; Phongtamrug, S.; Laobuthee, A. A simple, effective, and selective synthesis route without template effect (part II) for [2 + 2] difunctional 28-membered macrocyclic ethers based on benzoxazine dimers and its inclusion phenomena with metal ions. Chem. Lett. 2003, 5, 432-433. (Pubitemid 36930543)
10. Laobuthee, A.; Ishida, H.; Chirachanchai, S. Metal ion guest responsive benzoxazine dimers and inclusion phenomena of cyclic derivatives. J. Incl. Phenom. Macrocycl. Chem. 2003, 47, 179-185. (Pubitemid 39023804)
11. Chirachanchai, S.; Rungsimanon, T.; Phongtamrag, S.; Miyata, M.; Laobuthee, A. Selective Macrocyclization: A Model Case Study from N,N-bis(2-hydroxy-3,5-dimethylbenzyl)alkylamine. Tetrahedron 2009, 65, 5855-5861.
12. Chirachanchai, S.; Laobuthee, A.; Phongtamrag, S. Self termination of ring opening reaction of p-substituted phenol-based benzoxazines: An obstructive effect via intramolecular hydrogen bond. J. Heterocycl. Chem. 2009, 46, 714-721.
13. Kaewvilai, A.; Rungsimanon, T.; Koonsaeng, N.; Chirachanchai, S.; Laobuthee, A. Branching structures of alkali metal ion responsive supramolecules based on symmetric structures of N,N-bis(5-alkyl-2-hydroxybenzyl)methylamine. Asian J. Chem. 2010, 22, 7628-7640.
14. Holly, F.W.; Cope, A.C. Condensation Products of Aldehydes and Ketones with o-Aminobenzyl Alcohol and o-Hydroxybenzylamine. J. Am. Chem. Soc. 1944, 66, 1875.
15. Phongtamrug, S. Study on the benzoxazine monomers and their application for ion extraction material. Master Degree Thesis in Polymer Science; The Petroleum and Petrochemical College, Chulalongkorn University: Bangkok, Thailand, 1998.
16. Pedersen, C.J. Cyclic Polyesters and Their Complexes with Metal Salts. J. Am. Chem. Soc. 1967, 89, 1009-1020.
17. Pedersen, C.J.; Frensdorff, H.K. Macrocyclic polyethers and their complexes. Angew. Chem. Int. Ed. Engl. 1972, 11, 16.
18. Rakthin, T.; Veranitisagul, C.; Koonsaeng, N.; Traversa, E.; Laobuthee, A. Preparation of Ceria Powder via Metal-Organic Complex Method. In Proceedings of Pure and Applied Chemistry International Conference: Chemistry for Sufficiency and Sustainability, Amsterdam, The Netherlands, 22-23 February 2008; Parasuk, W., Ed.; Chemical Society of Thailand: Bangkok, Thailand, 2008; pp. 312-316.
19. 2) from Ce(III)-Benzoxazine Dimer Complexes via Thermal Decomposition. Int. J. Mol. Sci. 2011, 12, 4365-4377.
20. 2 Derived from Cerium Complexes as Solid Support Catalysts for Hydrogenations Reaction in a Micro-reactor. Energy Procedia 2011, 9, 568-574.
21. Accelrys Inc Materials Studio 5.5. Accelrys: San Diego, CA, USA.
22. Rappé, A.K.; Casewit, C.J.; Colwell, K.S.; Goddard, W.A.; Skiff, W.M. UFF, A Rule-Based Full Periodic Table Force Field for Molecular Mechanics and Molecular Dynamics Simulations. J. Am. Chem. Soc. 1992, 114, 10024.
23. Rappé, A.K.; Colwell, K.S.; Casewit, C.J. Application of a Universal Force Field to Metallic Complexes. Inorg. Chem. 1993, 32, 3438.
24. Rappé, A.K.; Goddard, W.A. Charge equilibration for molecular dynamics simulations. J. Phys. Chem. 1991, 95, 3358-3363.
25. Casewit, C.J.; Colwell, K.S.; Rappé, A.K. Application of a Universal Force Field to Organic Molecules. J. Am. Chem. Soc. 1992, 114, 10035.