Two Modes of Self-Coordinating Edge-over-Edge Zn(II) Porphyrin Dimerization:  A Structural and Spectroscopic Comparison

Stibrany, Robert T.; Vasudevan, Jayasree; Knapp, Spencer; Potenza, Joseph A.; Emge, and Tom; Schugar, Harvey J.

doi:10.1021/ja9536734

Cited by 106 publications

(58 citation statements)

References 20 publications

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“…A 2D-ROESY NMR experiment [4,16] performed at À 10 8C allowed the unambiguous assignment of all resonances. The nature of the overlap of the subunits in 1 is indicated by the pattern of shielding in which signals for protons closer to the coordinating amine appear at significantly higher field than those for otherwise similar protons.…”

Section: Communicationsmentioning

confidence: 99%

“…[20] Each zinc atom of the hexamer is apically coordinated to the secondary amino nitrogen atom of an adjoining monomer unit 7 to afford a square-pyramidal geometry similar to that in self-coordinating zinc(ii) porphyrin and bacteriochlorin dimers. [4,5] In contrast to the dimers, in which the porphyrin planes are approximately parallel and in p contact, the hexamer 8 features adjoining porphyrin ring p systems that are approximately orthogonal (Figure 4). This geometry is reminiscent of that in a polymeric oligomer of [10,15,20-triphenyl-5-(4-pyridyl)porphyrinato]zinc(ii) [22] and in other metalloporphyr- ins.…”

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confidence: 99%

“…[4] In the region of the Q bands the spectra of 7´DMAP and the dimer 1 are qualitatively similar. [17,18] , which are diagnostic for the four-coordinate zinc(ii) porphyrin monomer 7.…”

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confidence: 99%

“…This amine-tethered zinc(ii) porphyrin dimer exhibits mutual p overlap that is likewise limited to a single pyrrole ring. Dimers of zinc(ii) porphyrin [3,4] and bacteriochlorin [5] have been assembled by attaching a zinc-ligating heterocyclic substituent such as 2-pyridyl or 2-imidazolyl to a peripheral carbon atom of the chromophore. The natural tendency of porphyrinoids to p stack in parallel planes about 3.2 apart, [6] as well as the length, orientation, and point of attachment of the ligating tether, serve to position the p systems of the two rings in a stable dimeric arrangement that can be studied in solution.…”

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A Tethered Porphyrin Dimer with π Overlap of a Single Pyrrole Ring

Knapp

Vasudevan

Emge

et al. 1998

Angewandte Chemie International Edition

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Section: Communicationsmentioning

confidence: 99%

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“…[4] In the region of the Q bands the spectra of 7´DMAP and the dimer 1 are qualitatively similar. [17,18] , which are diagnostic for the four-coordinate zinc(ii) porphyrin monomer 7.…”

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A Tethered Porphyrin Dimer with π Overlap of a Single Pyrrole Ring

Knapp

Vasudevan

Emge

et al. 1998

Angewandte Chemie International Edition

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“…Thus, a number of pyridyl-and imidazolyl-substituted porphyrins exist in solutions in the form of dimeric supramolecular complexes [(ZnPy) 2 and (ZnIm) 2 ] having a 'slipped' orientation (14,15). The stronger the Zn -N L bond, the greater the degree of the dimerisation.…”

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confidence: 99%

Binding ability of Zn-tetraarylporphyrins with two, four and eight 4-(4-(3,6-bis(t-butyl)carbazol-9-ylphenyl)-1,2,3-triazole end groups towards N-containing substrates of different nature

Nguyen

Мамардашвили

Груздев

et al. 2012

Supramolecular Chemistry

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): Binding ability of Zn-tetraarylporphyrins with two, four and eight 4-(4-(3,6-bis(t-butyl)carbazol-9-ylphenyl)-1,2,3-triazole end groups towards N-containing substrates of different nature, Supramolecular Chemistry, 25:3,[180][181][182][183][184][185][186][187][188] To link to this article: http://dx.doi.org/10.1080/10610278.2012.741687 PLEASE SCROLL DOWN FOR ARTICLEFull terms and conditions of use: http://www.tandfonline.com/page/terms-and-conditions This article may be used for research, teaching, and private study purposes. Any substantial or systematic reproduction, redistribution, reselling, loan, sub-licensing, systematic supply, or distribution in any form to anyone is expressly forbidden.The publisher does not give any warranty express or implied or make any representation that the contents will be complete or accurate or up to date. The accuracy of any instructions, formulae, and drug doses should be independently verified with primary sources. The publisher shall not be liable for any loss, actions, claims, proceedings, demand, or costs or damages whatsoever or howsoever caused arising directly or indirectly in connection with or arising out of the use of this material.Binding ability of Zn-tetraarylporphyrins with two, four and eight 4-(4-(3,6-bis(t-butyl)carbazol-9-ylphenyl)-1,2,3-triazole end groups towards N-containing substrates of different nature The binding ability of Zn-tetraarylporphyrins with two, four and eight 4-carbazolylphenyl-1,2,3-triazole end groups towards 1,4-diazabicyclo[2.2.2]octane, pyridine and 1,2,3-triazole in toluene was studied by spectrophotometric and 1 H NMR titration. It was determined that due to a good geometric match of the ligand size to the size of the intramolecular cavities of the porphyrinic receptor, and by the existence of additional p-p and/or hydrogen bonding interactions between the ligand and the triazole fragments of the porphyrin, the Zn-tetraarylporphyrin with eight 4-carbazolylphenyl-1,2,3-triazole end groups could be used as an effective receptor for 1,2,3-triazole and other small heterocycles such as pyridine. Taking into account the fact that binding is accompanied by a clear and easily identifiable response in the UV -vis spectra of the reaction mixture, this metalloporphyrin could be considered as a molecular optical sensing device for small heterocyclic substrates.

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