Topochemical Polymerization of Phenylacetylene Macrocycles under Pressure

Year: 2018

Authors: Lapini A., Fanetti S., Citroni M., Bini R., Gilbert C.O., Rondeau-Gagne S., Morin J.F.

Autors Affiliation: [Lapini, Andrea; Fanetti, Samuele; Citroni, Margherita; Bini, Roberto] European Lab Nonlinear Spect LENS, Via Nello Carrara 1, I-50019 Florence, Italy.
[Lapini, Andrea] INO, Largo Fermi 6, I-50125 Florence, Italy.
[Fanetti, Samuele; Bini, Roberto] Univ Firenze, Dipartimento Chim Ugo Schiff, Via Lastruccia 3, I-50019 Florence, Italy.
[Gilbert, Charles-Olivier; Morin, Jean-Francois] Univ Laval, Dept Chim, 1045 Ave Med,Pavillon Alexandre Vachon, Quebec City, PQ G1V 0A6, Canada.
[Gilbert, Charles-Olivier; Morin, Jean-Francois] Univ Laval, Ctr Rech Mat Avances CERMA, 1045 Ave Med,Pavillon Alexandre Vachon, Quebec City, PQ G1V 0A6, Canada.
[Rondeau-Gagne, Simon] Univ Windsor, Dept Chem & Biochem, 401 Sunset Ave, Windsor, ON N9B 3P4, Canada.

Abstract: Self-assembly of organic macrocycles has been exploited as a preliminary step in the synthesis of soluble and tailorable carbon-based nanostructures. Functionalized nanotubes have been prepared using, as core building blocks, nearly planar ring structures containing several alkyne units, exploiting the geometry achieved in the spontaneous preassembling step driven by pi interaction. Covalent cross-linking between these units was achieved by thermal or photochemical activation with UV light. Here, we apply a moderate pressure in a sapphire anvil cell (1.0 GPa) to facilitate the preassembling and induce the cross-linking under pressure either with visible light, absorbed by two-photon absorption, or thermally. We observe a high yield of enhanced quality cross-linked nanotubes in a sample, showing, at ambient pressure, only side-chain decomposition. These results show that moderate pressures, easily achievable in large volume cells, are able to selectively favor topochemical reactions in such complex organic systems.


Volume: 122 (34)      Pages from: 20034  to: 20039

KeyWords: assembled diacetylene macrocycle; photoinduced reactivity; organic nanotubes; red phosphorus; water
DOI: 10.1021/acs.jpcc.8b06724

Citations: 4
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