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Volumn 7, Issue 2, 2003, Pages 112-119

Construction and complexation studies of some self-assembled diporphyrin receptors

Author keywords

Amines; Hydrogen bonding; Porphyrins; Supramolecular chemistry; UV vis spectroscopy

Indexed keywords

ALIPHATIC AMINE; AMINO ACID; AROMATIC AMINE; CARBOXYL GROUP; PORPHYRIN DERIVATIVE; UNCLASSIFIED DRUG; ZINC CARBOXYPHENYLPORPHYRIN DERIVATIVE;

EID: 0038753825     PISSN: 10884246     EISSN: None     Source Type: Journal    
DOI: 10.1142/S108842460300015X     Document Type: Article
Times cited : (7)

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    • and references therein
    • For porphyrin-based supramolecular receptors based on hydrogen bonding motifs see: a) Drain CM, Fischer R, Nolen EG and Lehn JM. J. Chem. Soc., Chem. Commun. 1993: 243-245. b) Kuroda Y, Kawashima A, Hayashi Y and Ogoshi H. J. Am. Chem. Soc. 1997; 119: 4929-4933. c) Guest-templated selection of noncovalent combinatorial assembling of porphyrin-based receptors have recently been reported: Calama MC, Timmerman P and Reinhoudt DN. Angew. Chem., Int. Ed. 2000; 39: 755-758, and references therein. For recent examples of self-assembling of porphyrin derivatives with potential features as receptor see: d) Ikeda C, Nagahara N, Motegi E, Yoshioka N and Inoue H. Chem. Commun. (Cambridge, U. K.) 1999: 1759-1760. e) Felluga F, Tecilla P, Hillier L, Hunter CA, Licini G and Scrimin P. Chem. Commun. (Cambridge, U. K.) 2000: 1087-1088.
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    • For porphyrin-based supramolecular receptors based on hydrogen bonding motifs see: a) Drain CM, Fischer R, Nolen EG and Lehn JM. J. Chem. Soc., Chem. Commun. 1993: 243-245. b) Kuroda Y, Kawashima A, Hayashi Y and Ogoshi H. J. Am. Chem. Soc. 1997; 119: 4929-4933. c) Guest-templated selection of noncovalent combinatorial assembling of porphyrin-based receptors have recently been reported: Calama MC, Timmerman P and Reinhoudt DN. Angew. Chem., Int. Ed. 2000; 39: 755-758, and references therein. For recent examples of self-assembling of porphyrin derivatives with potential features as receptor see: d) Ikeda C, Nagahara N, Motegi E, Yoshioka N and Inoue H. Chem. Commun. (Cambridge, U. K.) 1999: 1759-1760. e) Felluga F, Tecilla P, Hillier L, Hunter CA, Licini G and Scrimin P. Chem. Commun. (Cambridge, U. K.) 2000: 1087-1088.
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    • e) Porphyrin-based donor-acceptor systems assembled by electrostatic interactions have been recently reviewed: Sessler JL, Wang B, Springs SL and Brown CT. In Comprehensive Supramolecular Chemistry, Vol. 9, Atwood JL, Davies JE, Mac Nicol DD, Vogtle F. (Eds.) Elsevier: Oxford, 1996; pp 311-336.
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    • For some excellent, recent overviews on the role of hydrogen bonding in supramolecular chemistry see: a) Prins LJ, Reinhoudt DN and Timmerman P. Angew. Chem., Int. Ed. 2001; 40: 2383-2426. b) Sherrington DC and Taskinen KA. Chem. Soc. Rev. 2001; 30: 83-93.
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    • For some excellent, recent overviews on the role of hydrogen bonding in supramolecular chemistry see: a) Prins LJ, Reinhoudt DN and Timmerman P. Angew. Chem., Int. Ed. 2001; 40: 2383-2426. b) Sherrington DC and Taskinen KA. Chem. Soc. Rev. 2001; 30: 83-93.
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    • The UV-vis spectral changes, upon addition of this ligand to 2Zn, are similar to that observed for 4,4′-bpy. This indicates the occurrence of an interaction via coordination of both of nitrogen sites and, concomitantly, a 1:1 complex formation.
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    • a) Hunter CA and Sanders JKM. J. Am. Chem. Soc. 1990; 112: 5525-5534. For recent reports on the quantification of π-π stacking interactions in hydrogen bonding self assembled aromatic suprastructures see: b) Adams H, Hunter CA, Lawson KR, Perkins J, Spey SE, Urch CJ and Sanderson JM. Chem.Eur. J. 2001; 7: 4863-4877. c) Carver FJ, Hunter CA, Livingstone DJ, McCabe JF and Seward EM. Chem.Eur. J. 2002; 8: 2847-2859, and references therein.
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    • If a polymerisation was occurring in a linear fashion via a series of simple 1:1 binding events the apparent association constant would show only a moderate increase of K. For some recent examples related to porphyrin chemistry see: a) Twyman LJ and King ASH. Chem. Commun. (Cambridge, U. K.) 2002: 910-911. b) Drain CM, Shi XX, Milic T and Nifiatis F. Chem. Commun. (Cambridge, U. K.) 2001; 3: 287-288. c) For a quantitative approach to the problem see: Ercolani G. Chem. Commun. (Cambridge, U. K.) 2001: 1416-1417.
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    • Important studies on the enantioselective binding of aminoacid derivatives by a rigid diporphyrin cleft have been reported. See for example: a) Crossley MJ, Mackay LG and Try AC. J. Chem. Soc., Chem. Commun. 1995: 1925-1927. b) Crossley MJ, Hambley TW, Mackay LG, Try AC and Walton R. J. Chem. Soc., Chem. Commun. 1995: 1077-1079. For recent reports on asymmetric induction in multiporphyrin hydrogen-bonded assemblies see: c) Prins LJ, Huskens J, De Jong F, Timmerman P and Reinhoudt DN. Nature (London) 1999; 398: 498-502.
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    • Important studies on the enantioselective binding of aminoacid derivatives by a rigid diporphyrin cleft have been reported. See for example: a) Crossley MJ, Mackay LG and Try AC. J. Chem. Soc., Chem. Commun. 1995: 1925-1927. b) Crossley MJ, Hambley TW, Mackay LG, Try AC and Walton R. J. Chem. Soc., Chem. Commun. 1995: 1077-1079. For recent reports on asymmetric induction in multiporphyrin hydrogen-bonded assemblies see: c) Prins LJ, Huskens J, De Jong F, Timmerman P and Reinhoudt DN. Nature (London) 1999; 398: 498-502.
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