Neutral interlocked assemblies from anionic pseudorotaxanes coordinated to Sn(IV) and Cu(I) metallic centers

Baum, Robert R.; Veach, Jedidiah J.; Semeniuc, Radu F.; Wheeler, Kraig A.; Pellechia, Perry J.

doi:10.1016/j.ica.2016.10.006

Cited by 1 publication

(1 citation statement)

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“…Cu(I) and Sn(IV) pseudo[2]rotaxanes 73 (Figure ) were also recently synthesized, benefiting from the donor‐acceptor interaction between the BDNP 38 C 10 and the NDI axle, containing two anionic dithiophosphonate groups, and further reaction with (Ph 3 P) 2 CuNO 3 and R 3 SnCl (R=Me, Ph), respectively.…”

Section: Metallamacrocyclic and Interlocked Structuresmentioning

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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Section: Metallamacrocyclic and Interlocked Structuresmentioning

confidence: 99%