2003
DOI: 10.1016/s0040-4020(03)01128-1
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Self-aggregation of synthetic zinc 21-hydroxy-121/131-oxo-porphyrins

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Cited by 55 publications
(43 citation statements)
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“…Two zinc porphyrins possessing an OH and a C=O group at the 3/13-and 3/12-positions, respectively, have been investigated previously. [36] The former possesses a linear order of the chlorosomal moieties and self-aggregates, whereas the latter is bent slightly and forms no self-aggregates. The presence of a 13-C=O moiety in chlorosomal chlorin is therefore significant for such selfaggregation, and the orientation of this C=O moiety is also important for the formation of strong intermolecular interactions.…”
Section: Oligomeric States Of Zinc Chlorins 1-3: the 13-methoxycarbonmentioning
confidence: 99%
See 1 more Smart Citation
“…Two zinc porphyrins possessing an OH and a C=O group at the 3/13-and 3/12-positions, respectively, have been investigated previously. [36] The former possesses a linear order of the chlorosomal moieties and self-aggregates, whereas the latter is bent slightly and forms no self-aggregates. The presence of a 13-C=O moiety in chlorosomal chlorin is therefore significant for such selfaggregation, and the orientation of this C=O moiety is also important for the formation of strong intermolecular interactions.…”
Section: Oligomeric States Of Zinc Chlorins 1-3: the 13-methoxycarbonmentioning
confidence: 99%
“…), [24] and a C=O moiety (vide supra), and their linear situation along the Qy axis in a molecule (see arrow in the left drawing of Figure 1). [35,36] The strongest transition dipole moment in a chlorin chromophore is on the Qy axis, so parallel and slipped overlapping of the Qy axis in chlorins creates their J-aggregates, which give the above-mentioned red-shifts in the Qy absorption bands. We have previously reported that two representatives of the BChl models, zinc 3-(hydroxymethyl)-and 3-(1-hydroxyethyl)chlorins 5 [12] and 6, [22] respectively, easily form chlorosomal self-aggregates in an aqueous medium containing Triton X-100 (TX-100) as a surfactant, and that their stability and availability would be suitable for a composite molecule in an artificial lightharvesting system.…”
Section: Introductionmentioning
confidence: 99%
“…[7] Since our initial report, [5] Tamiaki's group, using an elegant synthesis, have implemented the same design principles to obtain the self-assembling octaethylporphyrin-derived porphyrin 17-Zn. [8] The authors rightly argue that 17-Zn, possessing only alkyl substituents, is more closely related than the meso-aryl-substituted porphyrins 12-ZnϪ16-Zn to the natural BChls. If practical applications are envisaged, [9] however, our compounds require fewer synthetic steps and so are more easily available, although octaethylporphyrin is a commercially available compound.…”
Section: Introductionmentioning
confidence: 99%
“…As judged from the broad, red-shifted absorption spectra, structurally very similar self-assembly patterns were obtained from 12-Zn, 13-Zn, 14-Zn, and 17-Zn. [5,8] These four compounds each have the hydroxy group (originating either from an achiral hydroxymethyl or from a 1-hydroxyethyl group), the zinc atom, and the carbonyl group arranged collinearly. A very intriguing result is that the isomeric zinc porphyrin 18-Zn failed to give red-shifted and broad absorption spectra upon self-assembly, which led the authors to speculate that collinearity of these three groups is an essential condition for the self-assembly to occur.…”
Section: Introductionmentioning
confidence: 99%
“…The self-assembly algorithm programmed within chlorosomes could be reproduced with completely artificial pigments (18)(19)(20)(21)(22), that lends hope that it can be used in solid-state devices such as hybrid solar cells (23,24). This would enable efficient light capturing and operation also under lowlight illumination conditions.…”
mentioning
confidence: 99%