Unveiling the nature of supramolecular crown ether–C<sub>60</sub> interactions

Moreira, Luis; Calbo, Joaquín; Calderón, Rafael M. Krick; Santos, José; Illescas, Beatriz M.; Aragó, Juan; Nierengarten, Jean‐François; Guldi, Dirk M.; Ortı́, Enrique; Martín, Nazario

doi:10.1039/c5sc00850f

Cited by 37 publications

(49 citation statements)

References 58 publications

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“…By means of plotting the normalized peak shifts, that is, for the first reduction of C 60 and the first oxidation of 1 a binding constant of 1.3×10 4 m −1 was derived with a 1:1 fitting function (Figure b). This value is comparable to those observed for the complexes of other DTF‐containing systems with fullerenes …”

Section: Resultssupporting

confidence: 86%

Dithiafulvenyl‐Extended N‐Heterotriangulenes and Their Interaction with C₆₀: Cooperative Fluorescence

Gliemann

Strauß

Hitzenberger

et al. 2017

Chemistry A European J

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We describe the synthesis as well as the electronic and photophysical characterization of novel N-heterotriangulene derivatives decorated with methoxycarbonyl-and methyl-sulfanyl-substituted dithiafulvenyl moieties. The association of these electron-richc ompounds with fullerene C 60 as electron acceptorw as investigated by meanso fp hotophysical, voltammetric,a nd mass spectrometric methods and rationalized by DFT calculations. Importantly,l ight-induced interactions between the dithiafulvene-substituted Nheterotriangulene bearing methoxycarbonyl substituents with C 60 leads to cooperative fluorescence. Quantitative Job plot analyses by means of fluorescences pectroscopy and voltammetry confirm a1 :1 association with binding constants in the order of 10 4 m À1.S upportive results for the supramolecular assembly of both N-heterotriangulenes with C 60 were obtainedb yE SI mass spectrometric investigations in the gas phase.

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Section: Resultssupporting

confidence: 86%

Dithiafulvenyl‐Extended N‐Heterotriangulenes and Their Interaction with C₆₀: Cooperative Fluorescence

Gliemann

Strauß

Hitzenberger

et al. 2017

Chemistry A European J

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“…If we turn our attention to fullerenes, C 60 and its derivatives, a large number of π‐conjugated electron‐donating systems are able to host the buckyball through π–π intermolecular interactions, a particular kind of NCIs. Among the different donor moieties employed, the truxene‐tetrathiafulvalene (truxTTF) system (Fig.…”

Section: Introductionmentioning

confidence: 99%

DLPNO-CCSD(T) scaled methods for the accurate treatment of large supramolecular complexes

et al. 2017

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In this work, we present scaled variants of the DLPNO-CCSD(T) method, dubbed as (LS)DLPNO-CCSD(T) and (NS)DLPNO-CCSD(T), to obtain accurate interaction energies in supramolecular complexes governed by noncovalent interactions. The novel scaled schemes are based on the linear combination of the DLPNO-CCSD(T) correlation energies calculated with the standard (LoosePNO and NormalPNO) and modified (Loose2PNO and Normal2PNO) DLPNO-CCSD(T) accuracy levels. The scaled DLPNO-CCSD(T) variants provide nearly TightPNO accuracy, which is essential for the quantification of weak noncovalent interactions, with a noticeable saving in computational cost. Importantly, the accuracy of the proposed schemes is preserved irrespective of the nature and strength of the supramolecular interaction. The (LS)DLPNO-CCSD(T) and (NS)DLPNO-CCSD(T) protocols have been used to study in depth the role of the CH-π versus π-π interactions in the supramolecular complex formed by the electron-donor truxene-tetrathiafulvalene (truxTTF) and the electron-acceptor hemifullerene (C H ). (NS)DLPNO-CCSD(T)/CBS calculations clearly reveal the higher stability of staggered (dominated by CH-π interactions) versus bowl-in-bowl (dominated by π-π interactions) arrangements in the truxTTF•C H heterodimer. Hemifullerene and similar carbon-based buckybowls are therefore expected to self-assemble with donor compounds in a richer way other than the typical concave-convex π-π arrangement found in fullerene-based aggregates. © 2017 Wiley Periodicals, Inc.

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“…68,[86][87][88][89] For instance, a guanidinium bis-ZnPor tweezers is able to form a hybrid with a C 60 -carboxylate - Fig. 17 -via hydrogen bonding as well as p-p stacking, featuring exceptionally high binding constants (10 6 M…”

Section: Artificial Photosynthesismentioning

confidence: 99%

A multicomponent molecular approach to artificial photosynthesis – the role of fullerenes and endohedral metallofullerenes

2016

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In this review article, we highlight recent advances in the field of solar energy conversion at a molecular level.We focus mainly on investigations regarding fullerenes as well as endohedral metallofullerenes in energy and/ or electron donor-acceptor conjugates, hybrids, and arrays, but will also discuss several more advanced systems. Hereby, the mimicry of the fundamental processes occurring in natural photosynthesis, namely light harvesting (LH), energy transfer (EnT), reductive/oxidative electron transfer (ET), and catalysis (CAT), which serve as a blue print for the rational design of artificial photosynthetic systems, stand at the focalpoint. Importantly, the key processes in photosynthesis, that is, LH, EnT, ET, and CAT, define the structure of this review with the only further differentiation in terms of covalent and non-covalent systems. Fullerenes as well as endohedral metallofullerenes are chosen by virtue of their small reorganization energies in electron transfer processes, on the one hand, and their exceptional redox behaviour, on the other hand.

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Unveiling the nature of supramolecular crown ether–C₆₀ interactions

Cited by 37 publications

References 58 publications

Dithiafulvenyl‐Extended N‐Heterotriangulenes and Their Interaction with C₆₀: Cooperative Fluorescence

Dithiafulvenyl‐Extended N‐Heterotriangulenes and Their Interaction with C₆₀: Cooperative Fluorescence

DLPNO-CCSD(T) scaled methods for the accurate treatment of large supramolecular complexes

A multicomponent molecular approach to artificial photosynthesis – the role of fullerenes and endohedral metallofullerenes

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Unveiling the nature of supramolecular crown ether–C60 interactions

Cited by 37 publications

References 58 publications

Dithiafulvenyl‐Extended N‐Heterotriangulenes and Their Interaction with C60: Cooperative Fluorescence

Dithiafulvenyl‐Extended N‐Heterotriangulenes and Their Interaction with C60: Cooperative Fluorescence

DLPNO-CCSD(T) scaled methods for the accurate treatment of large supramolecular complexes

A multicomponent molecular approach to artificial photosynthesis – the role of fullerenes and endohedral metallofullerenes

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Unveiling the nature of supramolecular crown ether–C₆₀ interactions

Dithiafulvenyl‐Extended N‐Heterotriangulenes and Their Interaction with C₆₀: Cooperative Fluorescence

Dithiafulvenyl‐Extended N‐Heterotriangulenes and Their Interaction with C₆₀: Cooperative Fluorescence