Results and Discussion
Synthesis of Tin(IV) Porphyrin-Viologen Dyad: Tin(IV)porphyrin-viologen dyads 1 & 2 (scheme 1) used in this study was synthesized by a series of reactions. 1-(4-Carboxybenzyl)-1'-methyl-4,4'-bipyridinium hexaflurophosphate was prepared from the reaction between 1-Methyl-4,4'-bipyridinium iodide with 4-(bromomethyl)benzoic acid followed by ion exchange with NH4PF6. Reaction of 1-(4-Carboxybenzyl)-1'-methyl-4,4'-bipyridinium hexaflurophosphate with [Sn(OH)2TPP] (TPP = tetraphenylporphyrin) and [Sn(OH)2TMPP] (TMPP = tetra-4-(2-(2-(2-methoxyethoxy)ethoxy)ethoxy) phenyl porphyrin) leads to the formation of 1 & 2 respectively. The two tin porphyrin derivatives were fully characterized by 1H NMR spectroscopy (Figure 1(a) and 4(a)) and 13C-NMR spectroscopy, as well as high-resolution mass spectrometry (see the Supporting Information). The resonances for the bipyridinium moiety of 1 appear sharply at 8.54 ppm with doublet patterns as well as a two singlet signal for N-CH3 at 4.37 and 4.76 ppm in the 1H NMR spectrum. On the other hand, the same peak appeared for 2 also.
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Scheme 1. Structure of the Sn(IV)porphyrin-viologen complexes 1 & 2 used in this study.
Supramolecular Complexation between 1 and 2 with …show more content…
The 1:2 ternary complexes of 2●CB[8] with HQ or HN shows a highly enhanced charge transfer interaction compare to 2●CB[8] itself. The major driving force for the large enhancement of the fluorescence spectra of the inclusion complexes are due to the charge transfer interaction between the electron rich guest and electron deficient 2●CB[8] as well as arises from their close contact within the CB[8] cavity.[9(b)] We now extended these type of inclusion complexes to other biological aromatic residues. The Fluorescence enhancement spectra due to the formation of inclusion complexes with Dopamine, Tyrosine and Tryptophan was given in the supplementary information (see figure S1, S2, and S3
Synthesis of Tin(IV) Porphyrin-Viologen Dyad: Tin(IV)porphyrin-viologen dyads 1 & 2 (scheme 1) used in this study was synthesized by a series of reactions. 1-(4-Carboxybenzyl)-1'-methyl-4,4'-bipyridinium hexaflurophosphate was prepared from the reaction between 1-Methyl-4,4'-bipyridinium iodide with 4-(bromomethyl)benzoic acid followed by ion exchange with NH4PF6. Reaction of 1-(4-Carboxybenzyl)-1'-methyl-4,4'-bipyridinium hexaflurophosphate with [Sn(OH)2TPP] (TPP = tetraphenylporphyrin) and [Sn(OH)2TMPP] (TMPP = tetra-4-(2-(2-(2-methoxyethoxy)ethoxy)ethoxy) phenyl porphyrin) leads to the formation of 1 & 2 respectively. The two tin porphyrin derivatives were fully characterized by 1H NMR spectroscopy (Figure 1(a) and 4(a)) and 13C-NMR spectroscopy, as well as high-resolution mass spectrometry (see the Supporting Information). The resonances for the bipyridinium moiety of 1 appear sharply at 8.54 ppm with doublet patterns as well as a two singlet signal for N-CH3 at 4.37 and 4.76 ppm in the 1H NMR spectrum. On the other hand, the same peak appeared for 2 also.
.
Scheme 1. Structure of the Sn(IV)porphyrin-viologen complexes 1 & 2 used in this study.
Supramolecular Complexation between 1 and 2 with …show more content…
The 1:2 ternary complexes of 2●CB[8] with HQ or HN shows a highly enhanced charge transfer interaction compare to 2●CB[8] itself. The major driving force for the large enhancement of the fluorescence spectra of the inclusion complexes are due to the charge transfer interaction between the electron rich guest and electron deficient 2●CB[8] as well as arises from their close contact within the CB[8] cavity.[9(b)] We now extended these type of inclusion complexes to other biological aromatic residues. The Fluorescence enhancement spectra due to the formation of inclusion complexes with Dopamine, Tyrosine and Tryptophan was given in the supplementary information (see figure S1, S2, and S3