Exceptionally Strong Electronic Communication through Hydrogen Bonds in Porphyrin–C<sub>60</sub> Pairs

Sánchez, Luis; Sierra, María; Martín, Nazario; Myles, Andrew J.; Dale, Trevor J.; Rebek, Julius; Seitz, W. Rudolf; Guldi, Dirk M.

doi:10.1002/anie.200601264

Cited by 118 publications

(69 citation statements)

References 56 publications

(6 reference statements)

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“…Moving to a more competitive medium, isothermal calorimetry (ITC), 13 C NMR experiments and molecular dynamics (MD) simulations all showed strong benzoate anion binding in 95 : 5 acetonitrile : water ( K a ∼ 2900 M –1 , 1 H NMR experiments were precluded by disappearance of N–H resonances in this solvent mixture, see ESI† for details of anion recognition experiments). 18 Negligible association was observed between 1 + and chloride anion in this competitive aqueous medium.…”

Section: Resultsmentioning

confidence: 82%

Supramolecular anion recognition in water: synthesis of hydrogen-bonded supramolecular frameworks

et al. 2017

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Section: Resultsmentioning

confidence: 82%

Supramolecular anion recognition in water: synthesis of hydrogen-bonded supramolecular frameworks

et al. 2017

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“…Photoexcitation of the fullerene chromophores to their 1.76-eV excited state is followed, in one of the three forms of 11, by a charge separation process generating a 1.15-eV radical ion pair state. On average, this state perdures for at least 1.5 s, which is comparable to the performance of other noncovalent C 60 -based hybrids (in which electron transfer occurs basically via through-space interactions) (14,15,(31)(32)(33) and is superior to that of typical covalent C 60 -exTTF conjugates (25)(26)(27)(28). The structure of 11 in principle allows its extension to form a nanotubular battery along which electron donors and electron acceptors alternate and also suggests the possibility of designing molecular switches based on dynamic control of interconversion between the electroactive isomer 11-Z and the inactive isomers 11-X and 11-Y.…”

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confidence: 52%

“…In fact, charge separation caused by photoexcitation of exTTF in either heterodimer 11 or homodimers of 10 is negligible, and an efficient electron transfer is precluded by the short lifetime (Ϸ0.86 ps) of the transient species with a spectral peak at 605 nm (SI Fig. 8) (31).…”

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confidence: 99%

Electron transfer in Me-blocked heterodimeric α,γ-peptide nanotubular donor–acceptor hybrids

Brea

Castedo

Granja

et al. 2007

Proc. Natl. Acad. Sci. U.S.A.

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Bio-inspired cyclopeptidic heterodimers built on ␤-sheet-like hydrogen-bonding networks and bearing photoactive and electroactive chromophores on the outer surface have been prepared. Different cross-strand pairwise relationships between the side chains of the cyclic ␣,␥-peptides afford the heterodimers as three nonequivalent dimeric species. Steady-state and time-resolved spectroscopies clearly show an electron transfer process from -extended tetrathiafulvalene, covalently attached to one of the cyclopeptides, to photoexcited [60]fullerene, located on the complementary cyclopeptide. The charge-separated state was stabilized for up to 1 s before recombining and repopulating the ground state. Our current example shows that cyclopeptidic templates can be successfully used to form light-harvesting/lightconverting hybrid ensembles with a distinctive organization of donor and acceptor units able to act as efficient artificial photosystems.cyclic peptide nanotubes ͉ fullerenes ͉ self-assembly P eptide-based tubular systems are being widely used to mimic Nature's channel-forming structures (1). Stable architectures ranging from ␤-helices to stacked macrocycles can self-assemble through multiple hydrogen-bonding interactions between and/or within peptide units with backbones capable of adopting an appropriate curvature. However, although a variety of versatile strategies have been developed to produce peptide tubes (2, 3), comparatively little has been done in the way of controlled functionalization of their inner and/or outer surfaces so as to fit them for specific tasks (4).Peptide nanotubes (PNs) or nanotube segments formed by the self-stacking of two or more cyclic peptides (2, 3, 5) are notable examples of the ''bottom-up'' approach to functional nanostructures. These self-assembled PNs have found application in biological and medical research and materials science (6-10). Their self-assembly is brought about by hydrogen bonding between their constituent cyclic peptides (CPs). The chirality of the amino acid residues of the CPs is such that the CP backbone forms an essentially flat ring with its CAO and NOH groups oriented nearly perpendicular to the ring plane and its side chains radiating outward. This conformation allows each face of the CP to take part in a ␤-sheet-like hydrogen-bond array with another CP that, depending on the sequence of amino acid residues in the CPs, must be oriented either parallel or antiparallel to the first (11-13). Scheme 1 shows an example of the antiparallel stacking of CPs formed of alternating ␣-and ␥-amino acid residues (␣,␥-CPs). Note that the precise orientation of side chains in planes perpendicular to the CP rings depends on backbone interactions within each ring.Within the nanobiomaterials field, one of the most actively pursued goals is the design of highly efficient and highly directional electron transfer mimics of the photosynthetic systems of plants and bacteria. In principle, self-assembled PNs bearing an appropriate array of photoactive and electroactive units might ac...

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“…Guldi et al reported a set of two-point amidinium-carboxylate H-bonded C 60 -porphyrin ensembles (8) [62]. between zinc porphyrin and C 60 was calculated.…”

Section: Electron Transfer Based On Double and Triple Hydrogen Bondingmentioning

confidence: 99%

Hydrogen Bonding-Controlled Photoinduced Electron and Energy Transfer

Chen

Tung

et al. 2015

Lecture Notes in Chemistry

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Photoinduced electron and energy transfer processes play an important role in photosynthesis and optoelectronic conversion. The investigation of photoinduced electron and energy transfer, wherein donor and acceptor are assembled via noncovalent interactions, has attracted much interest. Among these noncovalent interactions, H-bonding interaction has emerged as a powerful tool to construct high array of supramolecular architectures owing to their tunable binding constant, high directionality and selectivity. This chapter provides an overview of the recent developments in H-bonding-based energy/electron transfer. Advances in this research field, including (1) the basic theories for energy transfer and electron transfer processes, (2) recent progresses of energy transfer and electron transfer based on H-bonding, (3) their applications in constructing optoelectronic devices, light-harvesting systems, wide-range color display, and storage materials, are presented.

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Exceptionally Strong Electronic Communication through Hydrogen Bonds in Porphyrin–C₆₀ Pairs

Cited by 118 publications

References 56 publications

Supramolecular anion recognition in water: synthesis of hydrogen-bonded supramolecular frameworks

Supramolecular anion recognition in water: synthesis of hydrogen-bonded supramolecular frameworks

Electron transfer in Me-blocked heterodimeric α,γ-peptide nanotubular donor–acceptor hybrids

Hydrogen Bonding-Controlled Photoinduced Electron and Energy Transfer

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Exceptionally Strong Electronic Communication through Hydrogen Bonds in Porphyrin–C60 Pairs

Cited by 118 publications

References 56 publications

Supramolecular anion recognition in water: synthesis of hydrogen-bonded supramolecular frameworks

Supramolecular anion recognition in water: synthesis of hydrogen-bonded supramolecular frameworks

Electron transfer in Me-blocked heterodimeric α,γ-peptide nanotubular donor–acceptor hybrids

Hydrogen Bonding-Controlled Photoinduced Electron and Energy Transfer

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Exceptionally Strong Electronic Communication through Hydrogen Bonds in Porphyrin–C₆₀ Pairs