Synthesis and complexation study of new ExTTF-based hosts for fullerenes

Abstract

A new series of exTTF hosts has been synthesized for supramolecular binding study of fullerenes C60 and C70. Binding constants for C60 in chlorobenzene, toluene, toluene/CH2Cl2 and CS2 have been calculated for different hosts and a direct structure-affinity relationship has been established. As predicted, receptors with two exTTF moieties (1, 3 and 4) have demonstrated higher binding abilities toward C70 than C60. Depending on the linker used to attach the exTTF unit to the core of the host, different binding modes (1:1 and 2:1) have been obtained.

Carbon Nanotubes Conjugated with Triazole‐Based Tetrathiafulvalene‐Type Receptors for C60 Recognition

“…The titration of MWCNT‐2 with C 60 showed a similar behaviour: a decrease in the MWCNT absorption over 650 nm, with an isosbestic point at 630 nm (Figure , top). Nevertheless, the MWCNT lower absorption compared to SWCNT allowed the observation of a decrease in the intensity of the exTTF absorption at λ =438 nm, accompanied by the increase of a broad band in the 475–600 nm region, which matches the charge transfer from exTTF to C 60 observed in analogous molecular systems . Therefore, the formation of the supramolecular complex not only affects the absorption features of C 60 and exTTF, but also those of MWCNT and SWCNT, resulting in a decrease of their absorbances and the formation of new isosbestic points upon the addition of C 60 .…”

“…The preparation of single‐walled carbon nanotubes (SWCNT) and multi‐walled carbon nanotubes (MWCNT)‐based receptors for C 60 started with the synthesis of the exTTF tweezer receptor 4 , achieved by a Cu I ‐catalyzed 1,3‐dipolar cycloaddition followed by the conversion of the chloride 3 to the final azide (Scheme ). The reaction of 3,5‐bis(propargyloxy)benzyl chloride 1 and the azido‐containing exTTF 2 proceeded under standard conditions, in very low yields due to the precipitation of the monoaddition intermediate. The use of DMSO under microwave irradiation allowed to keep the intermediate solubilized during the reaction, and to synthesize chloride 3 with a 65 % yield.…”

The New 1,2,3-Triazolylantracene-9,10-Diones: Synthesis and ComputerBioactivity Screening

“…The new 1,2,3-triazole derivatives of 9,10-anthracendione 3-12 were obtained by the reaction of 1,3-dipolar azide-alkyne cycloaddition [1], which includes the interaction of freshly prepared azides AD-N 3 1,2 [13,14] (1,3-dipoles) with substituted acetylenes (dipolarofiles (Scheme 1, Table 1). The reaction of azides 1, 2 with phenylacetylene, propargyl alcohol and alkyl propiolates was carried out under conditions of copper(I)-catalyzed (CuAAC) reaction in the presence of trimethylamine.…”

“…1-azide-9,10-anthracenedione 1 [13], 2-azide-9,10-anthracenedione 2 [14], 1,4-and 1,5-diazido-9,10-anthracenediones 13,14 [15].…”

Synthetic Potential of 9,10-Anthraquinonyldiazonium Salts

“…The formation of 1(2)-azido derivatives of 9,10-anthracenedione easily occurs when the corresponding diazonium salts interact with sodium azide in an aqueous medium [10][11][12].…”