Macrocycles as Precursors for Organic Nanotubes

Pasini, Dario; Ricci, M.

doi:10.2174/157017907779981606

Cited by 72 publications

(35 citation statements)

References 45 publications

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“…Scientists exploit supramolecular chemistry (bottom-up strategy) to achieve this goal and control the organization of molecules into diverse 1D [2][3][4], 2D [5][6][7][8][9] or 3D shapes [10][11][12]. Owing to their directional potential, hydrogen bond [13][14][15][16][17][18][19][20][21][22][23] or halogen bond [24][25][26][27][28][29][30][31][32][33][34][35][36] are intermolecular forces that are often used to stick molecular building blocks together.…”

Section: Introductionmentioning

confidence: 99%

Isomorphous Crystals from Diynes and Bromodiynes Involved in Hydrogen and Halogen Bonds

et al. 2016

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Isomorphous crystals of two diacetylene derivatives with carbamate functionality (BocNH-CH 2 -diyne-X, where X = H or Br) have been obtained. The main feature of these structures is the original 2D arrangement (as supramolecular sheets or walls) in which the H bond and halogen bond have a prominent effect on the whole architecture. The two diacetylene compounds harbor neighboring carbamate (Boc protected amine) and conjugated alkyne functionalities. They differ only by the nature of the atom located at the penultimate position of the diyne moiety, either a hydrogen atom or a bromine atom. Both of them adopt very similar 2D wall organizations with antiparallel carbamates (as in antiparallel beta pleated sheets). Additional weak interactions inside the same walls between molecular bricks are H bond interactions (diyne-H¨¨¨O=C) or halogen bond interactions (diyne-Br¨¨¨O=C), respectively. Based on crystallographic atom coordinates, DFT (B3LYP/6-31++G(d,p)) and DFT (M06-2X/6-31++G(d,p)) calculations were performed on these isostructural crystals to gain insight into the intermolecular interactions.

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Section: Introductionmentioning

confidence: 99%

Isomorphous Crystals from Diynes and Bromodiynes Involved in Hydrogen and Halogen Bonds

et al. 2016

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“…A plethora of domains such as catalysis, photonics, material science, can also be targeted. [33][34][35][36] We have been particularly interested in synthesizing tubes through controlled stacking of sufficiently rigid ring units 1-4; each unit consisted of a macrolactam [37][38][39][40][41][42][43][44] of C n symmetry (n = 2, 3, 4, Figure 1). [45,46] Owing to the vast potential of such compounds we looked for expedient and efficient syntheses.…”

Section: Introductionmentioning

confidence: 99%

Efficient Synthesis and Astonishing Supramolecular Architectures of Several Symmetric Macrolactams

Baillargeon

Bernard

Gauthier

et al. 2007

Chemistry A European J

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The synthesis of four C(n) symmetric macrocyclic lactams cyclo-[NH-CH(2)-CH=CH-CH(2)-CO](n) (1, n=2; 2, n=3; 3, n=4) and cyclo-[NH-CH(2)-CH(2)-CH=CH-CO](3) (4) has been achieved by two approaches. A linear route leads to precursors that are subsequently macrocyclized in a separate step. The second, convergent approach relies on the symmetry of the targets: it includes suitably activated subunits, which are subjected to macrocyclization conditions. The subunits first oligomerize, then cyclize to form either pure macrolactams or mixtures. The macrolactam units 1, 2 and 4 stack on top each other through weak interactions (hydrogen bond and van der Waals), to form endless square, rectangular and triangular prisms, respectively. These stacks are further packed side by side in crystals grown from isotropic media. The overall dipoles in the crystals from lactams 1 and 4, which result mostly from the alignment of amide groups, are zero and large, respectively. Macrolactam 2 displays an astonishing isomorphism when allowed to cool down in anisotropic liquid crystal solutions. Large hollow hexagonal tubes are then obtained through a fractal process. Contrary to the three previous rings, 3 yields crystals where prisms of any shape are absent.

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“…One of the most appealing areas of research related to macrocyclic chemistry is their use as building blocks for the assembly of nanotubes [44,45,46]. Cyclic d , l -α-peptides, and more recently cyclic β 3 -peptides, have been shown to assemble into tubular structures through the association of complementary and suitably positioned amide hydrogen bonding units within the cyclic backbone [47].…”

Section: Peptide- and Sugar-containing Click Macrocyclesmentioning

confidence: 99%

The Click Reaction as an Efficient Tool for the Construction of Macrocyclic Structures

Pasini

2013

Molecules

Self Cite

123

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Abstract:The Cu(I)-catalyzed azide-alkyne cycloaddition (CuAAC, known as the click reaction) is an established tool used for the construction of complex molecular architectures. Given its efficiency it has been widely applied for bioconjugation, polymer and dendrimer synthesis. More recently, this reaction has been utilized for the efficient formation of rigid or shape-persistent, preorganized macrocyclic species. This strategy also allows the installment of useful functionalities, in the form of polar and function-rich 1,2,3-triazole moieties, directly embedded in the macrocyclic structures. This review analyzes the state of the art in this context, and provides some elements of perspective for future applications.

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Macrocycles as Precursors for Organic Nanotubes

Cited by 72 publications

References 45 publications

Isomorphous Crystals from Diynes and Bromodiynes Involved in Hydrogen and Halogen Bonds

Isomorphous Crystals from Diynes and Bromodiynes Involved in Hydrogen and Halogen Bonds

Efficient Synthesis and Astonishing Supramolecular Architectures of Several Symmetric Macrolactams

The Click Reaction as an Efficient Tool for the Construction of Macrocyclic Structures

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