Building large porphyrin arrays: pentamers and nonamers

Officer, David L.; Burrell, Anthony K.; Reid, David C. W.

doi:10.1039/cc9960001657

Cited by 62 publications

(37 citation statements)

References 11 publications

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“…Examples of dendritic multiporphyrin arrays include a vinylene‐linked nonameric dendritic nickel porphyrin array25 and a nonameric dendritic zinc porphyrin array with ethynylene and ester spacers 26. Compound 10 , which consists of an energy‐accepting free‐base porphyrin (P FB ) core decorated with eight energy‐donating zinc porphyrin (P Zn ) units, was later synthesized for photochemical studies 27.…”

Section: Dendritic Light‐harvesting Antennaementioning

confidence: 99%

Bioinspired Molecular Design of Light‐Harvesting Multiporphyrin Arrays

et al. 2003

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Recent progress in fundamental studies on multiporphyrin arrays has provided structural parameters for the molecular design of artificial light-harvesting antennae which mimic the wheel-like antenna complexes of photosynthetic purple bacteria. Covalent and noncovalent approaches have been employed for the construction of artificial light-harvesting multiporphyrin arrays. Such arrays are categorized into ring-shaped, windmill-shaped, star-shaped, and dendritic architectures. In particular, dendritic multiporphyrin arrays have been proven to be promising candidates for both providing a large absorption cross-section and enabling the vectorial transfer of energy over a long distance to a designated point. Such molecular and supramolecular systems are also expected to be potent components for molecular electronics and photonic devices.

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Section: Dendritic Light‐harvesting Antennaementioning

confidence: 99%

Bioinspired Molecular Design of Light‐Harvesting Multiporphyrin Arrays

et al. 2003

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“…Beispiele für dendritische Multiporphyrinsysteme umfassen ein Vinylen‐verknüpftes nonameres dendritisches Nickelporphyrinsystem25 und ein nonameres dendritisches Zinkporphyrinsystem mit Ethinylen‐ und Esterspacern 26. Das Dendrimer 10 , bestehend aus einem P FB ‐Energieacceptor im Kern und acht peripheren P Zn ‐Energiedonoreinheiten, wurde für photochemische Studien synthetisiert 27.…”

Section: Dendritische Lichtsammelantennenunclassified

Bioinspiriertes Molekulardesign von lichtsammelnden Multiporphyrinsystemen

Choi

Yamazaki

et al. 2003

Angewandte Chemie

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Jüngste Fortschritte bei Grundlagenstudien zu Multiporphyrinsystemen geben Aufschluss über die maßgeblichen Strukturparameter für das Molekulardesign von künstlichen Lichtsammelantennen, die die radähnlichen Antennenkomplexe photosynthetischer Purpurbakterien imitieren. “Kovalente” und “nichtkovalente” Ansätze kamen für den Aufbau von künstlichen lichtsammelnden Multiporphyrinsystemen zum Einsatz. Diese lassen sich in die Kategorien ring‐, windmühlen‐, sternförmig und dendritisch einteilen, wobei insbesondere die dendritischen Multiporphyrinsysteme als vielversprechende Kandidaten gelten. Sie verfügen über einen hohen Absorptionsquerschnitt und ermöglichen einen zielgerichteten vektoriellen Energietransfer über große Entfernungen. Erwartet wird, dass sich solche molekularen und supramolekularen Systeme als leistungsstarke Komponenten für die molekulare Elektronik und in photonischen Bauelementen eignen.

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“…38 Tetraarylporphyrins are generally prepared by the condensation of pyrrole with a benzaldehyde. As mono building block 34 is effectively just a functionalized benzaldehyde and reacted so well with the dipyrrylmethane 64, the condensation reactions with pyrrole were examined.…”

Section: Arrays Consisting Of Five Porphyrinsmentioning

confidence: 99%

Functionalizing Porphyrins via Wittig Reactions: A Building Block Approach

Burrell

Officer

1998

Synlett

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IntroductionTetrapyrrolic macrocycles play a number of critical biological roles such as: molecular binding, reaction catalysis, electron transfer, energy transfer and light-harvesting. The importance of these functions has provided the impetus for intensive research towards artificial systems that may be able to model or mimic their natural counterparts.One of the major difficulties in duplicating the natural systems has been the difficulties encountered synthetically replicating the specific tetrapyrrolic macrocycles. Most work has concentrated on the porphyrins as these are generally more readily prepared and have greater stability than the other tetrapyrrolic macrocycles. As a result a number of research groups have invested significant resources in the synthesis of specific porphyrin systems, resulting in many cases in truly elegant synthetic procedures. For our research program in functional materials, the lure of porphyrins was too great for us to resist. However, the available porphyrin synthetic methodologies were not appropriate for our purposes. Therefore, we tackled the problem of preparing functionalized porphyrins with a very general approach. What we were looking for was an ubiquitous porphyrin starting material that could be prepared in high yield, with minimum effort. We imposed a couple of other rules upon ourselves. The first, and the most important, being to avoid syntheses that require the separation of statistical mixtures. Secondly, we wanted a system where the porphyrin core was covalently connected to the attached functionality. Abstract:The development of porphyrins functionalized by the CH 2 PPh 3 Cl moiety has enabled a range of new porphyrins to be conveniently prepared. This is best demonstrated by their utility in the preparation of building blocks for large porphyrin arrays. Examples, of the utility of these phosphonium salt porphyrins and their derivatives are presented herein.

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Building large porphyrin arrays: pentamers and nonamers

Abstract: A building block approach towards porphyrin arrays is used to construct pentameric and nonameric porphyrin arrays in one step.

Cited by 62 publications

References 11 publications

Bioinspired Molecular Design of Light‐Harvesting Multiporphyrin Arrays

Bioinspired Molecular Design of Light‐Harvesting Multiporphyrin Arrays

Bioinspiriertes Molekulardesign von lichtsammelnden Multiporphyrinsystemen

Functionalizing Porphyrins via Wittig Reactions: A Building Block Approach

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