Cyclodipeptide-bridged porphyrin dimer supramolecular assemblies

Kim, Dong-Yong; Heo, Jeonghun; Ham, Sujin; Yoo, Hyejin; Lee, Chi Hwa; Yoon, Hongsik; Ryu, Duyeol; Kim, Dongho; Jang, Woo Dong

doi:10.1039/c0cc04654j

Cited by 19 publications

(18 citation statements)

References 41 publications

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“…A typical sample of H 2 TPP is a nonaggregated molecule with a typical electronic absorption spectrum in CHCl 3 with a Soret band at λ =418 nm and Q absorption bands at λ =517, 551, 590, and 646 nm 5d. 7 However, from the results given in Figure 4 A, the absorption spectrum of H 2 TPP‐POSS in CHCl 3 has a clear shoulder at λ =376 nm, which indicates a typical “face‐to‐face” stacking mode (H‐type aggregate) between porphyrin moieties with a planar construction 6. Additionally, with increasing concentration, both the Soret and Q absorption bands broaden; moreover, the absorption intensity at λ =418 nm does not increase linearly with concentration at concentrations over 6.6×10 −6 M (inset of Figure 4 A), which indicates that π–π stacking occurs between porphyrin moieties.…”

Section: Resultsmentioning

confidence: 96%

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Morphology‐Controlled Self‐Assembly of an Organic/Inorganic Hybrid Porphyrin Derivative Containing Polyhedral Oligomeric Silsesquioxane (POSS)

Liu

Zhang

2015

Chemistry A European J

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An organic/inorganic hybrid porphyrin derivative, namely, metal-free tetrakisphenyl porphyrin-polyhedral oligomeric silsesquioxanes (H2 TPP-POSS) was synthesized by azide-alkyne click chemistry. The self-assembly behavior of H2 TPP-POSS was systematically studied in CHCl3 at different concentrations and in solvents with different polarities. Novel nanovesicles could be obtained through the self-assembly of H2 TPP-POSS in CHCl3 at a concentration lower than 10(-4) m. Diffuse microrods formed at a concentration higher than 10(-4) M. Additionally, the polarity of the solvent also greatly influenced the assembled morphologies, and a series of assembled morphologies, including crescent-shaped micelles, spherical micelles, doughnut-shaped vesicles, and ordered square sheets, could form in solvents with different polarities.

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Section: Resultsmentioning

confidence: 96%

“…For example, Jang et al. studied the supramolecular assembly of a cyclodipeptide‐bridged porphyrin dimer, and obtained both fibrous and toroidal assembled structures through variation in the solvent concentration 6. Cai et al.…”

Section: Introductionmentioning

confidence: 99%

Morphology‐Controlled Self‐Assembly of an Organic/Inorganic Hybrid Porphyrin Derivative Containing Polyhedral Oligomeric Silsesquioxane (POSS)

Liu

Zhang

2015

Chemistry A European J

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“…Kim et al synthesized a conjugate comprising two hydrophobic porphyrins linked by the dipeptide YY, which was subsequently cyclized into the corresponding diketopiperazine derivative (conjugate 22) [72]. The appearance of a strong and broad CD band around 375 nm highlights H-aggregates formation and concentration-dependent self-assembly of this specie in toluene.…”

Section: Other Dipeptidesmentioning

confidence: 99%

Peptide-Tetrapyrrole Supramolecular Self-Assemblies: State of the Art

et al. 2021

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The covalent and noncovalent association of self-assembling peptides and tetrapyrroles was explored as a way to generate systems that mimic Nature’s functional supramolecular structures. Different types of peptides spontaneously assemble with porphyrins, phthalocyanines, or corroles to give long-range ordered architectures, whose structure is determined by the features of both components. The regular morphology and ordered molecular arrangement of these systems enhance the photochemical properties of embedded chromophores, allowing applications as photo-catalysts, antennas for dye-sensitized solar cells, biosensors, and agents for light-triggered therapies. Chemical modifications of peptide and tetrapyrrole structures and control over the assembly process can steer the organization and influence the properties of the resulting system. Here we provide a review of the field, focusing on the assemblies obtained from different classes of self-assembling peptides with tetrapyrroles, their morphologies and their applications as innovative functional materials.

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“…Kim et al showed the formation of chromophore assays by a cyclic peptide‐bridged porphyrin dimer . The dimer was synthesized by symmetric substitution of the cyclodipeptide by porphyrins.…”

Section: Self‐assembly Of Peptide–chromophore Conjugatesmentioning

confidence: 99%

Peptide‐Modulated Self‐Assembly of Chromophores toward Biomimetic Light‐Harvesting Nanoarchitectonics

et al. 2015

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Elegant self-assembling complexes by the combination of proteins/peptides with functional chromophores are decisively responsible for highly efficient light-harvesting and energy transfer in natural photosynthetic systems. Mimicking natural light-harvesting complexes through synthetic peptides is attractive due to their advantanges of programmable primary structure, tunable self-assembly architecture and easy availability in comparison to naturally occuring proteins. Here, an overview of recent progresses in the area of biomimetic light-harvesting nanoarchitectonics based on peptide-modulated self-assembly of chromophores is provided. Adjusting the organization of chromophores, either by creating peptide-chromophore conjugates or by the non-covalent assembly of peptides and chromophores are highlighted. The light-harvesting properties, especially the energy transfer of the biomimetic complexes are critically discussed. The applications of such complexes in the mineralization of inorganic nanoparticles, generation of molecular hydrogen and oxygen, and photosynthesis of bioactive molecules are also included.

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Cyclodipeptide-bridged porphyrin dimer supramolecular assemblies

Abstract: A cyclodipeptide-bridged porphyrin dimer has formed fibrous and toroidal multi-porphyrin array systems by hydrogen bonding-mediated self-assembly.

Cited by 19 publications

References 41 publications

Morphology‐Controlled Self‐Assembly of an Organic/Inorganic Hybrid Porphyrin Derivative Containing Polyhedral Oligomeric Silsesquioxane (POSS)

Morphology‐Controlled Self‐Assembly of an Organic/Inorganic Hybrid Porphyrin Derivative Containing Polyhedral Oligomeric Silsesquioxane (POSS)

Peptide-Tetrapyrrole Supramolecular Self-Assemblies: State of the Art

Peptide‐Modulated Self‐Assembly of Chromophores toward Biomimetic Light‐Harvesting Nanoarchitectonics

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