Affinity modulation of photoresponsive hosts for fullerenes: light-gated corannulene tweezers

Barbero, Héctor; Ferrero, Sergio; Álvarez‐Miguel, Lucía; Gómez‐Iglesias, Patricia; Miguel, Daniel; Álvarez, Celedonio M.

doi:10.1039/c6cc06445k

Cited by 26 publications

(22 citation statements)

References 56 publications

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“…Corannulene, for instance, binds to C 60 34,35 and its incorporation in receptors enables their binding to fullerenes. [36][37][38] It is also involved in applications derived from its self-association such as liquid crystals, 39 organogelators, 40 and supramolecular polymer formation. 41 Besides, self-aggregation studies of hydrophilic analogues of corannulene functionalized with nucleosides allowed for an uncommon examination in water media.…”

Section: Introductionmentioning

confidence: 99%

Heptagon-Containing Saddle-Shaped Nanographenes: Self-Association and Complexation Studies with Polycyclic Aromatic Hydrocarbons and Fullerenes

et al. 2021

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Supramolecular interactions between molecules of the same or different nature determine to a great extent the degree of their applicability in many fields of science. To this regard, planar polycyclic aromatic hydrocarbons (PAHs) and their nanometric congeners, nanographenes (NGs), as well as positively curved ones, as for instance corannulene, have been extensively explored. However, negatively curved saddle-shaped NGs have remained a curiosity to date within this field. Therefore, here we communicate the first systematic study on the supramolecular behavior of heptagon-containing hexa-peri-hexabenzocoronene analogues. Thus, their self-association and host–guest complexation processes with both flat and curved PAHs, and fullerenes have been studied by means of 1H and 13C NMR titrations in solution, identifying C70 as one of the guests with the highest association constant among all the ones tested.

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Section: Introductionmentioning

confidence: 99%

Heptagon-Containing Saddle-Shaped Nanographenes: Self-Association and Complexation Studies with Polycyclic Aromatic Hydrocarbons and Fullerenes

et al. 2021

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“…In contrast with nonplanar PAH-based approaches, no discrimination between C 60 and C 70 has been reported for pyrene-based systems. This is quite surprising because current supramolecular approaches require more complex scaffolds based on nonplanar PAHs such as corannulene moieties, which are not easily synthetically accessible. Achieving a good balance between facile synthesis and a high affinity constant and, in particular, the ability to achieve discrimination still remains challenging.…”

Section: Introductionmentioning

confidence: 99%

Dual-Tweezer Behavior of an Octapodal Pyrene Porphyrin-Based System as a Host for Fullerenes

et al. 2019

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The incorporation of eight pyrene units in a single porphyrin core exhibits a great synergistic effect, resulting in high affinity towards C 60 and C 70. This octapyrene porphyrin is easily accessible by a straightforward two-step synthetic approach that involves an octuple Suzuki reaction. The new supramolecular platform can present single or double tweezer fullerene hosting behavior. The switch from double to single tweezer behaviour is triggered by the simple coordination of Zn 2+ to the porphyrin. Both the octa-pyrene porphyrin 2HPOP and its zinc metalloporphyrin analogue ZnPOP show very high affinity for C 60 and C 70 , while simultaneously allowing the discrimination of C 70 over C 60 in a C 60 /C 70 mixture. The use of 2HPOP and ZnPOP for the enrichment of real fullerene mixtures is also demonstrated.

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“…In contrast, development of buckybowl‐containing materials with desirable properties is still in its infancy. For instance, during the 50 years since the discovery of the first solution route for corannulene preparation (1966), only around 20 papers include any photophysical studies, despite nearly 1000 publications focused on corannulene. To the best of our knowledge, there are only two reports in the area of corannulene solid‐state photophysics.…”

Section: Methodsmentioning

confidence: 99%

Hierarchical Corannulene‐Based Materials: Energy Transfer and Solid‐State Photophysics

et al. 2017

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We report the first example of a donor–acceptor corannulene‐containing hybrid material with rapid ligand‐to‐ligand energy transfer (ET). Additionally, we provide the first time‐resolved photoluminescence (PL) data for any corannulene‐based compounds in the solid state. Comprehensive analysis of PL data in combination with theoretical calculations of donor–acceptor exciton coupling was employed to estimate ET rate and efficiency in the prepared material. The ligand‐to‐ligand ET rate calculated using two models is comparable with that observed in fullerene‐containing materials, which are generally considered for molecular electronics development. Thus, the presented studies not only demonstrate the possibility of merging the intrinsic properties of π‐bowls, specifically corannulene derivatives, with the versatility of crystalline hybrid scaffolds, but could also foreshadow the engineering of a novel class of hierarchical corannulene‐based hybrid materials for optoelectronic devices.

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Affinity modulation of photoresponsive hosts for fullerenes: light-gated corannulene tweezers

Cited by 26 publications

References 56 publications

Heptagon-Containing Saddle-Shaped Nanographenes: Self-Association and Complexation Studies with Polycyclic Aromatic Hydrocarbons and Fullerenes

Heptagon-Containing Saddle-Shaped Nanographenes: Self-Association and Complexation Studies with Polycyclic Aromatic Hydrocarbons and Fullerenes

Dual-Tweezer Behavior of an Octapodal Pyrene Porphyrin-Based System as a Host for Fullerenes

Hierarchical Corannulene‐Based Materials: Energy Transfer and Solid‐State Photophysics

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