Preparation of Neutral [60]Fullerene‐Based [2]Catenanes and [2]Rotaxanes Bearing an Electron‐Deficient Aromatic Diimide Moiety

Nakamura, Yosuke; Minami, Satoshi; Iizuka, Kazuki; Nishimura, Jun

doi:10.1002/ange.200351411

Cited by 14 publications

(5 citation statements)

References 67 publications

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“…A synthetic strategy based on π–π interactions was used by Nakamura and co‐workers to prepare fullerene‐rotaxane architectures. The interaction between an electron‐poor naphthalenetetracarboxylic diimide with an electron‐rich 1,5‐dihydroxynaphthalene, yielded a pseudorotaxane.…”

Section: Rotaxane‐fullerene Architecturesmentioning

confidence: 99%

Carbon Nanostructures in Rotaxane Architectures

2019

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Section: Rotaxane‐fullerene Architecturesmentioning

confidence: 99%

Carbon Nanostructures in Rotaxane Architectures

2019

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“…The [60]fullerene acted as stopper in 58 or electron‐acceptor unit in 59 . The syntheses of both 58 and 59 were performed starting from the corresponding mono‐stopped axle, using the Bingel reaction, in the presence of BDNP 38 C 10 and an excess of fullerene …”

Section: Catenanes and Rotaxanesmentioning

confidence: 99%

Naphthalenediimide – A Unique Motif in Macrocyclic and Interlocked Supramolecular Structures

et al. 2018

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This review presents as urvey through macrocyclic andi nterlocked structures containing 1,4,5,8-naphthalendiimide residues from the synthetic point of view and also illustrates the structural particularities that dictate their main applications in supramolecular, biological and materials chemistry. Thep aper is organised as ac omprehensived escription of macrocycles,c yclophanes,c atenanes,r otaxanes and metallamacrocyclesa long with other types of supramolecular interlockeda rchitectures.F or each category,w ep resent the synthetic approach, the structural investigation of their properties and the developed applications as semiconductors, energy storage devices,p hotovoltaics,a rtificial photosystems,sensors,catalysts or molecular machines. 1I ntroduction 2C yclophanes andMacrocycles 3C atenanes andRotaxanes 4M etallamacrocyclic andI nterlocked Structures 5O ther Complex Interlocked Structures 6C onclusions 1I ntroductionArylenediimides (ADIs) are ac lass of aromatic, redox-active compounds showing good thermal, chemical and photochemicals tability that found importanta pplications in various fields ranging from biological chemistry to supramolecular chemistry and materials sciences. [1][2][3][4][5][6][7][8] Pyrromelliticdiimides (PMDIs), naphthalenediimides (NDIs) and perylenediimides (PDIs) are the most studied compounds of this class.Althought he first reports regarding the synthesis and photoelectronic properties of NDI derivatives can be found in the early 1970s, [9] the real potentialo f these compounds was recognized only at the endo f the last century.T he NDI derivatives have lately emerged as the hottest topic among the arylenediimides and became the most investigated in this class. This is reasoned by their enhanced photophysical and redox properties,c omparedt oP MDIsa sw ell as their improved solubility comparedtoP DIs. [6] Structurally,N DI is ap lanar molecule containinga hydrophobic naphthalene core functionalized at positions 1, 4, 5a nd 8w ith twoe lectron-withdrawing imide groups that decrease the charge density on the naphthalene moiety,r esulting in highly acidic p-sur-face.T hese structural elements made NDI an appealing building block for the construction of complex supramoleculara rchitectures associated by p-p stacking, charge-transfer (CT) and van derW aals interactions that involve the naphthalene residue,h ydrogen bonding involving aromatic C-H and C=Og roups,a s well as metal-coordination to the imide groups. [10][11][12][13] N,N-Functionalized NDI derivatives are readily accessible by treatment of 1,4,5,8-naphthalenetetracarboxylic acid dianhydride (NDA) with aliphatic or aromatic amines,i np olars olvents such as DMF or N,Ndimethylacetamide,a th igh temperatures. [14] Simple NDI chromophores display intense absorption bands, in DCM, at wavelengths lower than 400 nm, and weak emission bands,w ith shortS tokes shifts and low quantum yields.M oreover, NDI derivatives have low LUMO energy levels (i.e., À3.7eVf or N,N-dioctylnaphthalenediimide) andc an easily undergo two oneelectronr ev...

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“…The properties of fullerenes derive from the three‐dimensional structure of their extended π system that makes them excellent electron acceptors and chromophores. Initially, fullerenes were introduced in catenanes,23, 24 pseudorotaxanes,25 and rotaxanes24, 26–29 (Scheme ) as a synthetic challenge, as fullerenes present a low solubility in many solvents and are hard to process, but always with the short‐term objective of exploiting their inherent properties.…”

Section: Interlocked Architectures Equipped With C60mentioning

confidence: 99%

Fullerenes: Multitask Components in Molecular Machinery

et al. 2007

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Molecular machines are molecular-scale devices that carry out predetermined tasks derived from molecular motion. This Minireview illustrates how fullerenes can be used as multitask building blocks in molecular machinery, providing new perspectives for fullerenes. Indeed, C(60) can be applied as a photo- and electroactive stopper owing to its size, as a probe for molecular motion as a result of its well-defined physicochemical properties, and to induce motion through pi-pi interactions. Such molecular motion can be employed to modulate light-driven electron-transfer events, extending the potential applications of molecular machines to the typical fields of application of fullerenes.

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Preparation of Neutral [60]Fullerene‐Based [2]Catenanes and [2]Rotaxanes Bearing an Electron‐Deficient Aromatic Diimide Moiety

Cited by 14 publications

References 67 publications

Carbon Nanostructures in Rotaxane Architectures

Carbon Nanostructures in Rotaxane Architectures

Naphthalenediimide – A Unique Motif in Macrocyclic and Interlocked Supramolecular Structures

Fullerenes: Multitask Components in Molecular Machinery

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