Abstract
A molecular tweezer incorporating two acridinium moieties linked by a 1,3-dipyridylbenzene spacer was synthesized in three steps. The formation of its self-complementary dimer in water was demonstrated as a result of π-π stacking and hydrophobic interactions. Moreover, a 1 : 1 mixture of this bis-acridinium tweezer with one built on a 2,6-diphenylpyridyl spacer evidenced its narcissistic self-sorting behaviour in water.
Highlights
To cite this version: Henri-Pierre Jacquot de Rouville, Christophe Gourlaouen, Valérie Heitz
A molecular tweezer incorporating two acridinium moieties linked by a 1,3-dipyridylbenzene spacer was synthesized in three steps
We recently described the synthesis of a self-complementary bis-acridinium tweezer (1∙2Cl) in a five-step synthesis (Scheme 1).[13]
Summary
A molecular tweezer incorporating two acridinium moieties linked by a 1,3-dipyridylbenzene spacer was synthesized in three steps. Comparison of the 1H NMR spectrum of 2∙2Cl (c = 3 x 10‒3 mol L‒1) to our previously reported bis-acridinium receptor 1∙2Cl showed analogous chemical shifts for the acridinium protons ( (H1/8) = 7.98 , (H2/7) = 7.88, (H3/6) = 8.45 and (H4/5) = 8.90 ppm, see Fig. 1a-b).[13] This observation suggests that the acridinium protons of 2·2Cl are not affected by the electronic environment of the aromatic ring (phenyl or pyridyl) at their 9-position. After evaporation of the solvent and solubilisation in D2O, the recorded spectrum was identical to the former 1H NMR spectrum in D2O (see ESI, Fig. S3.4) These additional experiments clearly demonstrate that this self-sorted mixture is under thermodynamic control.[20] it can be inferred that in D2O, more than 95% of the mixture is composed of both dimers meaning that the association constant of (1)2∙4Cl is at least ten times higher than that of (2)2∙4Cl. Fig. These [N∙∙∙H] distances are shorter in (1)24+ than in (2)24+ suggesting a stronger binding between linkers in (1)24+ in accordance with the highest driving force for the selfassociation of homodimer (1)24+
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