

Synthons for supramolecular assemblies: Synthesis of new triazine-core polyhydroxylated and multi-N-donor compounds
Muhammad Moazzam Naseer (1,*)



(1) Department of Chemistry, Quaid-i-Azam University, Islamabad-45320, Pakistan
(2) Department of Biochemistry, Pir Mehr Ali Shah Arid Agriculture University, Rawalpindi, Pakistan
(3) Department of Chemistry, Quaid-i-Azam University, Islamabad-45320, Pakistan
(*) Corresponding Author
Received: 15 Feb 2013 | Revised: 02 Mar 2013 | Accepted: 13 Mar 2013 | Published: 30 Jun 2013 | Issue Date: June 2013
Abstract
The synthesis of new triazine-core polyhydroxylated and multi-N-donor compounds are being reported. The reaction of 2,4,6-tris(4-n-butylaminophenyl)triazine (1) with cyanuric chloride provided star-shaped fragment (2) with six reactive chloro-substituents. Upon treatment of this fragment with bis(2-hydroxyethyl)amine (3a) and bis(2-pyridylmethyl)amine (3b), functionalized polyhydroxylated (4a) and multi-N-donor compounds (4b) were obtained in high yields through nucleophilic aromatic substitution. These functionalized compounds are expected to have unique applications in supramolecular self-assembly and material chemistry.

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DOI: 10.5155/eurjchem.4.2.149-152.750
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Funding information
The higher education commission (HEC), (PM-IPFP/HRD/HEC/2011/3407), Govt. of Pakistan, Pakistan
References
[1]. Naseer, M. M.; Hameed, S. Cryst. Eng. Comm. 2012, 14, 4247-4250.
http://dx.doi.org/10.1039/c2ce25118c
[2]. Leininger, S.; Olenyuk, B.; Stang, P. J. Chem. Rev. 2000, 100, 853-907.
http://dx.doi.org/10.1021/cr9601324
PMid:11749254
[3]. Northrop, B.; Zheng, Y. R.; Chi, K. W.; Stang, P. J. Acc. Chem. Res. 2009, 42, 1554-1563.
http://dx.doi.org/10.1021/ar900077c
PMid:19555073 PMCid:2764814
[4]. Li, S. S.; Northrop, B.; Yuan, Q. H.; Wan, L. J.; Stang, P. J. Acc. Chem. Res. 2009, 42, 249-259.
http://dx.doi.org/10.1021/ar800117j
PMid:19072706 PMCid:2654282
[5]. Pluth, M. D.; Bergman, R. G.; Raymond, K. N. Science 2007, 316, 85-88.
http://dx.doi.org/10.1126/science.1138748
PMid:17412953
[6]. Rebek J. Jr. Acc. Chem. Res. 2009, 42, 1660-1668.
http://dx.doi.org/10.1021/ar9001203
PMid:19603810
[7]. Tiefenbacher, K.; Rebek, J. Jr. J. Am. Chem. Soc. 2012, 134, 2914-2917.
http://dx.doi.org/10.1021/ja211410x
PMid:22263583
[8]. Tiefenbacher, K.; Ajami, D.; Rebek, J. Jr. Angew. Chem. Int. Ed. 2011, 50, 12003-12007.
http://dx.doi.org/10.1002/anie.201102548
PMid:22002600 PMCid:3272346
[9]. Desiraju. G. R. Angew. Chem. Int. Ed., 1995, 34, 2311-2327.
[10]. Gondi, S. R.; Son, D. Y. Synth. Commun. 2004, 34, 3061-3072.
http://dx.doi.org/10.1081/SCC-200028517
[11]. Black, C. T.; Ruiz, R.; Breyta, G.; Cheng, J. Y.; Colburn, M. E.; Guarini, K. W.; Kim, H. C.; Zhang, Y. IBM J. Res. Dev. 2007, 51, 605-633.
http://dx.doi.org/10.1147/rd.515.0605
[12]. Fendler, J. H. Chem. Mater. 2001, 13, 3196-3210.
http://dx.doi.org/10.1021/cm010165m
[13]. Zhang, S.; Marini, D. M.; Hwang, W.; Santoso, S. Curr. Opin. Chem. Biol. 2002, 6, 865-871.
http://dx.doi.org/10.1016/S1367-5931(02)00391-5
[14]. Otsuka, H.; Nagasaki, Y.; Kataoka, K. Curr. Opin. Colloid Interface Sci. 2001, 6, 3-10.
http://dx.doi.org/10.1016/S1359-0294(00)00082-0
[15]. Chen, W.-Y.; Ouyang, L.; Chen, R.-Y.; Li, X.-S. Synth. Commun. 2012, 42, 2585-2594.
http://dx.doi.org/10.1080/00397911.2011.563023
[16]. Arai, T.; Yamada, Y.; Yamamoto, N.; Sasai, H.; Shibasaki, M. Chem. Eur. J. 1996, 2, 1368-1372.
http://dx.doi.org/10.1002/chem.19960021107
[17]. Weis, M.; Waloch, C.; Seiche, W.; Breit, B. J. Am. Chem. Soc. 2006, 128, 4188-4189.
http://dx.doi.org/10.1021/ja058202o
PMid:16568968
[18]. Stojanovic, M. N.; De Prada, P.; Landry, D. W. J. Am. Chem. Soc. 2000, 122, 11547-11548.
http://dx.doi.org/10.1021/ja0022223
[19]. Yang, X.; Johnson, S.; Shi, J.; Holesinger, T.; Swanson, B. Sens. Actuators B 1997, 45, 79-84.
http://dx.doi.org/10.1016/S0925-4005(97)00273-6
[20]. Yang, H.; Yu, C.; Song, Q.; Xia, Y.; Li, F.; Chen, Z.; Li, X.; Yi, T.; Huang, C. Chem. Mater. 2006, 18, 5173-5177.
http://dx.doi.org/10.1021/cm061112d
[21]. Jiang, S. P.; Liu, Z.; Tian, Z. Q. Adv. Mater. 2006, 18, 1068-1072.
http://dx.doi.org/10.1002/adma.200502462
[22]. Yoshizawa, M.; Klosterman, J. K.; Fujita, M. Angew. Chem., Int. Ed. 2009, 48, 3418-3438.
http://dx.doi.org/10.1002/anie.200805340
PMid:19391140
[23]. Hof, F.; Craig, S. L.; Nuckolls, C.; Rebek, J. Angew. Chem., Int. Ed. 2002, 41, 1488-1508.
http://dx.doi.org/10.1002/1521-3773(20020503)41:9<1488::AID-ANIE1488>3.0.CO;2-G
[24]. Lindoy, L. F.; Atkinson, I. M. Self-Assembly in Supramolecular Systems (Monographs in Supramolecular Chemistry), Volume 7, Royal Society of Chemistry, Cambridge, 2000.
[25]. Fujita, M. Molecular Self Assembly: Organic Versus Inorganic Approaches. Structure and Bonding, Volume 96, Springer, Berlin, 2000.
[26]. Megger, D. A.; Muller, J. Synth. Commun. 2011, 41, 2524-2529.
http://dx.doi.org/10.1080/00397911.2010.505704
[27]. Fiedler, D.; Leung, D. H.; Bergman, R. G.; Raymond, K. N. Acc. Chem. Res. 2005, 38, 351-360.
http://dx.doi.org/10.1021/ar040152p
PMid:15835881
[28]. Kusukawa, T.; Nakai, T.; Okano, T.; Fujita, M. Chem. Lett. 2003, 32, 284-285.
http://dx.doi.org/10.1246/cl.2003.284
[29]. Schaefer, F. C.; Peters, G. A. J. Org. Chem. 1961, 26, 2778-2784.
http://dx.doi.org/10.1021/jo01066a036
[30]. Juarez, R.; Gomez, R.; Segura, J. L.; Seoane, C. Tetrahedron Lett. 2005, 46, 8861-8864.
http://dx.doi.org/10.1016/j.tetlet.2005.10.073
[31]. Naseer, M. M.; Wang, D.-X.; Zhao, L.; Huang, Z.-T.; Wang, M.-X. J. Org. Chem. 2011, 76, 1804-1813.
http://dx.doi.org/10.1021/jo102483x
PMid:21291201
[32]. Naseer, M. M.; Hameed, S. Appl. Organometal. Chem. 2012, 26, 330-334.
http://dx.doi.org/10.1002/aoc.2865
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DOI Link: https://doi.org/10.5155/eurjchem.4.2.149-152.750

















European Journal of Chemistry 2013, 4(2), 149-152 | doi: https://doi.org/10.5155/eurjchem.4.2.149-152.750 | Get rights and content
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