Synthesis, Electrochemical and Photophysical Properties, and Electroluminescent Performance of the Octa‐ and Deca(aryl)[60]fullerene Derivatives

Matsuo, Yutaka; Sato, Yoshiharu; Hashiguchi, Masaaki; Matsuo, Kazuya; Nakamura, Eiichi

doi:10.1002/adfm.200900021

Cited by 49 publications

(35 citation statements)

References 38 publications

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“…Although FVP is capable of building up strain energy of such magnitudes, 34 Herges and coworkers reported the failure of an attempt to close the walls of the picotube pyrolytically at 800 1C (Scheme 11). 36 Instead of cyclodehydrogenation, the pyrolysis reaction led to a mixture of products, in most of which the quinoid bonds and the neighboring single bonds were cleaved (52,53,54). An unexpected rearrangement also took place, affording an odd conjugated belt ( 51) that includes a seven-membered ring, probably formed in a radical mechanism.…”

Section: Approaches Based On Flash Vacuum Pyrolysis (Fvp)mentioning

confidence: 99%

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Synthetic approaches to aromatic belts: building up strain in macrocyclic polyarenes

2010

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This tutorial review discusses synthetic strategies towards aromatic belts, defined here as double-stranded conjugated macrocycles, such as [n]cyclacenes, [n]cyclophenacenes, Schlüter belt, and Vögtle belt. Their appeal stems, firstly, from the unique nature of their conjugation, having p orbitals oriented radially rather than perpendicular to the plane of the macrocycle. Secondly, as aromatic belts are model compounds of carbon nanotubes of different chiralities, a synthetic strategy towards the buildup of structural strain in these compounds could finally open a route towards rational chemical synthesis of carbon nanotubes. The elusiveness of these compounds has stimulated fascinating and ingenious synthetic strategies over the last decades. The various strategies are classified here by their approach to the buildup of structural strain, which is the main obstacle in the preparation of these curved polyarenes.

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Section: Approaches Based On Flash Vacuum Pyrolysis (Fvp)mentioning

confidence: 99%

“…53 In another recent work, it was demonstrated how a [10]cyclophenacene derivative, together with two other multifunctionalized organo[60]fullerenes, could be embedded in p-conjugated polymers to create an organic electroluminescent diode device that emits white light. 54…”

Section: Fullerene-derived [10]cyclophenacenementioning

confidence: 99%

Synthetic approaches to aromatic belts: building up strain in macrocyclic polyarenes

2010

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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: 77%

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

et al. 2017

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Abstract:We report the first example of ad onor-acceptor corannulene-containing hybrid material with rapid ligand-toligand energy transfer (ET). Additionally,weprovide the first time-resolved photoluminescence (PL) data for any corannulene-based compounds in the solid state.C omprehensive 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,w hich are generally considered for molecular electronics development. Thus,the presented studies not only demonstrate the possibility of merging the intrinsic properties of p-bowls, specifically corannulene derivatives,w ith the versatility of crystalline hybrid scaffolds,b ut could also foreshadowt he engineering of anovel class of hierarchicalcorannulene-based hybrid materials for optoelectronic devices.While the compromise between strain and aromaticity is ap ersistent synthetic challenge, [1][2][3] the bowl shape and electronic properties of corannulene derivatives (buckybowls, Scheme 1) imply an unrevealed potential for molecular electronics development similar to their close famous analogues,fullerenes.The main success of the latter in the field of optoelectronics is associated with very fast energy/electron transfer, which has been demonstrated in numerous photophysical studies. [4][5][6] In contrast, development of buckybowlcontaining materials with desirable properties is still in its infancy. Fori nstance,d uring the 50 years since the discovery of the first solution route for corannulene preparation (1966), [1] only around 20 papers [2, include any photophysical studies,d espite nearly 1000 publications focused on corannulene.T othe best of our knowledge,there are only two reports [8,10] in the area of corannulene solid-state photophysics.F urthermore,n os olid-state time-resolved photoluminescence (PL) data or energy transfer (ET) studies have been reported for any corannulene-containing compounds despite the fact that ET rate and efficiency are crucial fundamental parameters for applications ranging from organic photovoltaics to photocatalysis. [33,34] This gap in material development was the major driving force to initiate the presented study,especially taking into account the recent progress in corannulene chemistry. [35] Our shift from more traditional flat aromatic hydrocarbons [36] towards p-bowls (for example,c orannulene) was also driven by 1) their significant dipole moment, 2) the possibility to extend the dimensionality of 3D hybrid frameworks through the p-bowl curvature,3 )potential for charge stabilization on the surface owing to doubly degenerate lowest unoccupied molecular orbitals (LUMOs), 4) anticipated effective intermolecular charge transport, and 5) presence of theoretically predicted super atomic molecular orbitals,w hich are key factors for intermolecular charge/ energy transport distinct from the c...

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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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Synthesis, Electrochemical and Photophysical Properties, and Electroluminescent Performance of the Octa‐ and Deca(aryl)[60]fullerene Derivatives

Cited by 49 publications

References 38 publications

Synthetic approaches to aromatic belts: building up strain in macrocyclic polyarenes

Synthetic approaches to aromatic belts: building up strain in macrocyclic polyarenes

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

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

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