Rigid organic nanotubes obtained from phenylene-butadiynylene macrocycles

Abstract

Rigid organic nanotubes were prepared from six-membered phenylene-butadiynylene macrocycles through topochemical polymerization in the xerogel state. All six butadiyne units underwent polymerization, thus creating rigid nanotubes with six polydiacetylene chains lying parallel, one relative to each other.

Oligoyne Derivatives as Reactive Precursors for the Preparation of Carbon Nanomaterials

“…30 The difference between these and macrocycles from the PAM family is that PBMs possess six buta-1,3-diyne units in the macrocyclic scaffold. If the topochemical polymerization proceeds with all six butadiyne units, it will lead to very unique molecular architectures in which six PDA chains lay parallel relative to each other, forming semiconducting symmetrical nanotubes with high rigidity.…”

“…Inversely, the PAMs with the benzamide configuration adopt a nonstaggered, face-to-face configuration that allows the topo- More recently, we pushed the concept of macrocycles cross-linking a little further by preparing nanotubes from phenylene-butadiynylene macrocycles (PBMs). 30 The difference between these and macrocycles from the PAM family is that PBMs possess six buta-1,3-diyne units in the macrocyclic scaffold. If the topochemical polymerization proceeds with all six butadiyne units, it will lead to very unique molecular architectures in which six PDA chains lay parallel relative to each other, forming semiconducting symmetrical nanotubes with high rigidity.…”

Binaphthyl-Based Macrocycles as Optical Sensors for Aromatic Diphenols

“…Those features are fundamental properties to be sought in order to enhance the recognition/complexation properties toward suitable inclusion guests. This issue is also stringent because macrocycles can self-assemble in stable organic nanotubes by supramolecular organization in the third dimension [5][6][7].…”

Spontaneous Capture of Carbohydrate Guests through Folding and Zipping of Self‐Assembled Ribbons

“…Shape-persistent aromatic macrocycles have as trong tendency to stack on top of each other to generate columnar fibrils that laterally associate to form various higher order structures. [14] Therefore,w ee xpected that the cyclohexa-mphenylene unit generates long fibrils surrounded by flexible chains,w hich are able to further associate in as ide-by-side fashion. To control the lateral association of the elementary columnar stacks and endow the molecules with amphiphilic features,w ei ncorporated ah ydrophilic oligoether dendron into the aromatic periphery.A mphiphilic molecule 1,b ased on adiscotic macrocycle,was synthesized from commercially available starting materials according to the procedures reported previously (Supporting Information, Figures S1 and S2).…”