Synthese von Sulfolenobilinen und deren Cyclisierung zu Chlorinatozink-Fulleren-Dyaden

Kutzki, Olaf; Walter, A.; Montforts, Franz‐Peter

doi:10.1002/1522-2675(20000906)83:9<2231::aid-hlca2231>3.0.co;2-s

Cited by 25 publications

(16 citation statements)

References 7 publications

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“…Former investigations demonstrated that pyrroles can be attached with an aldehyde function to nickel tripyrrin intermediate 5 and that carboxylate groups in the opposite α‐position allow cyclization of the initially formed bilins to chlorins (Scheme ). [6a]…”

Section: Resultsmentioning

confidence: 99%

“…But then formylations of cyano‐substituted pyrroles fail due to the strong electron withdrawing effect of the cyano function . [6a],…”

Section: Resultsmentioning

confidence: 99%

“…Detailed investigations on chlorin fullerene dyad 3a and its zinc complex 3b by Smirnov revealed their unusual photophysical properties , . With dyad 4b envisaged in this work the influence of the distance between donor and acceptor in the dyad should be further investigated.…”

Section: Introductionmentioning

confidence: 83%

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Synthesis of a Chlorin Fullerene Dyad for Artificial Photosynthesis

Bertran

Montforts

2017

Eur J Org Chem

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To mimic photosynthesis a new chlorin fullerene dyad 4b was synthesized. Chlorin donor and fullerene acceptor subunits were linked by means of a Diels–Alder reaction. The chlorin donor moiety represents the characteristic chromophore of chlorophylls. Nature and evolution has optimized chlorophylls to be efficient light‐harvesting pigments. Artificial photosynthesis devices should also benefit from this evolutionary optimization. The rigid spacer and quite extended spacer geometry of 4b was chosen to minimize electron interaction between the chlorin donor and the fullerene acceptor.

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Section: Resultsmentioning

confidence: 99%

“…But then formylations of cyano‐substituted pyrroles fail due to the strong electron withdrawing effect of the cyano function . [6a],…”

Section: Resultsmentioning

confidence: 99%

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Synthesis of a Chlorin Fullerene Dyad for Artificial Photosynthesis

Bertran

Montforts

2017

Eur J Org Chem

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“…The dyads have shown promising results in molecular device applications for efficient conversion of light to electrostatic energy, , and they are considered good model systems of natural photosynthesis. ,, However, the natural photosynthesis utilizes chlorophylls in the reaction center, where the primary charge separation takes place, and as antenna molecules . As these harvest light with higher efficiency relative to fully conjugated porphyrins, it is quite surprising that relatively few DA dyads have been synthesized where a chlorophyll-like donor, instead of porphyrin, has been linked with fullerene. − The photochemical properties of some chlorin−fullerene dyads have been recently characterized. − ,, Chlorin−fullerene systems can undergo photoinduced ET in solutions 15,16,20,21 and in solid state. ,, …”

Section: Introductionmentioning

confidence: 99%

The Role of the Exciplex State in Photoinduced Electron Transfer of Phytochlorin−[60]Fullerene Dyads

et al. 2002

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The photoinduced electron transfer (ET) in five structurally different phytochlorin-fullerene dyads was studied in polar and nonpolar solvents using femtosecond fluorescence up-conversion and pump-probe transientabsorption techniques. Small changes in the structures of the dyads result in considerable changes in the ET properties and allow the determination of reorganization energies of the photoinduced reactions and electronic couplings between the initial and final states. After the excitation of the phytochlorin moiety to the second excited singlet state, the dyads relax rapidly to the first excited singlet state of phytochlorin. The first excited singlet state of phytochlorin is in equilibrium with an intramolecular exciplex state. In polar benzonitrile, the exciplex undergoes an electron transfer, and a complete-charge-separated (CCS) state is formed with a quantum yield close to unity. In contrast to the previously studied phytochlorin-fullerene dyads, the dyads in the present study form the CCS state also in nonpolar toluene with a yield influenced by minor changes in the molecular structure. The new dyads have a weaker phytochlorin-fullerene interaction due to longer separation distances between the two moieties. Therefore, the energies of the exciplex states are increased, and thus, their formation rates are reduced. In addition, the rates and yields of the complete charge separations are increased both in polar and nonpolar solvents. In benzonitrile, the reorganization energies for the transitions from the exciplex to the CCS and from the CCS to the ground state are 0.38 and 1.05 eV, respectively. The electronic couplings between the corresponding initial and final states of the two transitions mentioned above are 22 and 15 cm -1 .

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“…In particular, the combination with [60]fullerene, has led to very interesting materials [1][2][3][4][5][6][7][8]. It comes as no surprise that chlorins were utilized extensively in electron-tranfer studies because such compounds can be regarded as model compounds for the photosynthetic reaction center with a naturally occuring electron-donor [9][10][11][12][13][14][15][16][17][18]. In all of these contributions, the chlorin was either attached via an azomethine ylide addition [9][10][11] or by a Diels-Alder reaction approach [12][13][14][15][16][17][18].…”

Section: Introductionmentioning

confidence: 99%