Synthetic Routes to Multiporphyrin Arrays

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

doi:10.1021/cr0000426

Cited by 413 publications

(218 citation statements)

References 241 publications

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“…Dyad 13a with a singly bridged diporphyrin shows a photophysical behavior similar to that reported in the literature for other porphyrin-fullerene donor-acceptor systems [73][74][75][76][77][78]86]. Upon excitation of the diporphyrin at 530 nm in toluene at 298 K, the porphyrin luminescence is quenched due to photoinduced electron transfer to the fullerenes under formation of a luminescent CT state with a lifetime of 630 ps and an emission maximum at 953 nm.…”

Section: Extended Porphyrin-fullerene Conjugatessupporting

confidence: 68%

“…Porphyrin-fullerene conjugates are intensely investigated as electron donor-acceptor dyads and triads, in which porphyrin donors lose their characteristic luminescence properties as a result of light-induced energy and/or electron transfer to the fullerene acceptor [73][74][75][76][77][78]. On the other hand, Osuka and coworkers have introduced new oligoporphyrin arrays in which the porphyrin rings are either linked by single bonds in a biaryl-type fashion or triply fused under generation of porphyrin sheets with exceptional electronic properties [79][80][81].…”

Section: Extended Porphyrin-fullerene Conjugatesmentioning

confidence: 99%

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Advanced opto-electronics materials by fullerene and acetylene scaffolding

Diederich

2005

Pure and Applied Chemistry

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Functional π-systems with unusual opto-electronic properties are intensively investigated from both fundamental research and technological application viewpoints. This article reports on novel π-conjugated systems obtained by acetylenic and fullerene scaffolding. Linearly conjugated acetylenic nanorods, consisting of monodisperse poly(triacetylene) (PTA) oligomers and extending up to 18 nm length, were prepared to investigate the limits of effective conjugation and to explore at which length a monodisperse oligomer reaches the properties of an infinite polydisperse polymer. With the cyanoethynylethenes (CEEs), a powerful new class of electron acceptors is introduced that undergo intense intramolecular charge-transfer (CT) interactions with appended donors. Macrocyclic scaffolds with unusual opto-electronic properties are perethynylated dehydroannulenes, expanded radialenes, and radiaannulenes bearing peripheral dialkylanilino donor groups. Extended porphyrin-fullerene conjugates are investigated for their novel photophysical and efficient multicharge storage properties. Self-assembly of fullerenes and porphyrins, governed by weak interactions between the two components, leads to unprecedented nanopatterned surfaces that are investigated by scanning tunneling microscopy (STM).

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Section: Extended Porphyrin-fullerene Conjugatessupporting

confidence: 68%

Section: Extended Porphyrin-fullerene Conjugatesmentioning

confidence: 99%

Advanced opto-electronics materials by fullerene and acetylene scaffolding

Diederich

2005

Pure and Applied Chemistry

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“…(PPIX)Zn was found to be sensitive to room light and would decompose in less than 24 h. With this knowledge, the porphyrin (DPP)Zn replaced the (PPIX)Zn molecule. This non-natural molecule was intentionally chosen because it serves as a basic building block in more complex porphine systems that have a wide array of functionalities and applications such as: nonlinear optics, molecular beacons, biomolecular imaging reagents and lightharvesting antennae [34][35][36][37][38][39] .…”

Section: Resultsmentioning

confidence: 99%

Photoinitiated charge separation in a hybrid titanium dioxide metalloporphyrin peptide material

et al. 2014

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In natural systems, electron flow is mediated by proteins that spatially organize donor and acceptor molecules with great precision. Achieving this guided, directional flow of information is a desirable feature in photovoltaic media. Here, we design self-assembled peptide materials that organize multiple electronic components capable of performing photoinduced charge separation. Two peptides, c16-AHL 3 K 3 -CO 2 H and c16-AHL 3 K 9 -CO 2 H, self-assemble into fibres and provide a scaffold capable of binding a metalloporphyrin via histidine axial ligation and mineralize titanium dioxide (TiO 2 ) on the lysine-rich surface of the resulting fibrous structures. Electron paramagnetic resonance studies of this self-assembled material under continuous light excitation demonstrate charge separation induced by excitation of the metalloporphyrin and mediated by the peptide assembly structure. This approach to dye-sensitized semiconducting materials offers a means to spatially control the dye molecule with respect to the semiconducting material through careful, strategic peptide design.

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“…Covalent multiporphyrin arrays are attracting interest as multichromophoric model systems for the study of electron transfer process in natural photosynthetic systems, as well as in the development of novel functional materials [13]. Various types of covalently linked arrays of metallo porphyrins have been designed and synthesized with the goal of applying these molecular oligomers to molecular photonic devices [26,52,[59][60][61][62] as artificial light-harvesting systems [34,[62][63][64][65].…”

Section: Meso-meso Linked Porphyrin Arraysmentioning

confidence: 99%

“…Porphyrins comprise an important area of research interest in organic chemistry due to their potential in wide range of applications including light-harvesting arrays [13,14], molecular wires [15][16][17][18], photovoltaic cells [19], nonlinear optics [20][21][22][23], and photodynamic therapy [24]. Porphyrins are interesting in view of visible-light (Soret band around 400 nm and Q-band around 500-700 nm) absorbing and emitting materials as candidates for the study of electron and energy transfer processes to serve as artificial photosynthetic building units as well as for opto-electronic applications [25].…”

Section: Multiporphyrins As Chemical Models For Photosynthesismentioning

confidence: 99%

Meso-Linked Multiporphyrins as Model for Light Harvesting Systems: Review

Singhal¹

2017

Nat Prod Chem Res

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Nature has always been the fundamental source of inspiration for researchers to understand the complex biological functions. Photosynthesis is among the important natural phenomena and hence, gained interest towards developing the artificial photosynthetic reaction centers. Electron and energy transfer process between various porphyrin units within the multiporphyrin arrays is the important key in developing such systems. Long duration of charge separated state and spectral coverage scope of the accepting porphyrin units are another important factor that contribute to an efficient mimic of the photosynthetic reaction center. Meso-linked porphyrin architectures provide a great aspect in this regard because of short inter-porphyrinic distance with optimal dihedral angle. The present review highlights the design of various kinds of meso-linked multiporphyrins and study of electron and energy transfer processes between them that serve as an efficient model for light harvesting systems.

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Synthetic Routes to Multiporphyrin Arrays

Cited by 413 publications

References 241 publications

Advanced opto-electronics materials by fullerene and acetylene scaffolding

Advanced opto-electronics materials by fullerene and acetylene scaffolding

Photoinitiated charge separation in a hybrid titanium dioxide metalloporphyrin peptide material

Meso-Linked Multiporphyrins as Model for Light Harvesting Systems: Review

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