Cu(I)-catalysed azide-alkyne cycloaddition reactions were used to functionalise lanthanide(III)-complexes (Ln; La, Eu and Tb) incorporating alkyne or azide reactive groups. Microwave irradiation significantly accelerated the reactions, enabling full conversion to the triazole products in some cases in 5 min. Alkyl and aryl azides and alkyl and aryl alkynes could all serve as coupling partners. These reaction conditions proved efficient for cyclen-tricarboxylates and previously unreactive cyclen-tris-primary amide chelates. The synthesis of heterobimetallic (Eu/Tb, EuTb17 and Eu/La, EuLa17) and heterotrimetallic (Eu/La/Eu) complexes was achieved in up to 60% isolated yield starting from coumarin 2-appended alkynyl complexes Tb16 or La16 and an azido-Eu complex Eu4, and bis-alkynyl La-complex La5 and Eu4, respectively. EuTb17 displayed dual Eu(III) and Tb(III)-emission upon antenna-centred excitation.
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Strength enhancement of nanostructured organogels through inclusion of phthalocyanine-containing complementary organogelator structures and in situ cross-linking by click chemistry.
Chemistry
December 2008
The Dow Chemical Company, Dow Europe GmbH, Bachtobelstrasse 3, 8810 Horgen, Switzerland.
Stable photoactive organogels were successfully prepared by a two-step sequence involving: 1) formation of thermoreversible organogels by use of a combination of low-molecular-weight organogelators (LMOGs) and ZnII-phthalocyanine (ZnII-Pc) moieties containing complementary organogelator structures, and 2) strength enhancement of the gels by in situ cross-linking with the aid of CuI-catalysed azide-alkyne [3+2] cycloadditions (CuAACs). The optimum click reaction was carried out between a flexible C6 aliphatic diazide and a suitable dialkyne (molar ratio 1:1) added in a low proportion relative to the organogelator system [LMOG+ZnIIPc]. The dialkyne unit was incorporated into a molecule resembling the LMOGs structure in such a way that it could also participate in the self-assembly of [LMOG+ZnIIPc].
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