By Ulrich S. Schubert, Andreas Winter, George R. Newkome
Lately, the usage of terpyridines either in macromolecular constitution meeting and machine chemistry has exploded, allowing, for instance, supramolecular polymer architectures with switchable chemical and actual homes in addition to novel practical fabrics for optoelectronic functions reminiscent of light-emitting diodes and sunlight cells. extra functions contain using terpyridines and their steel complexes as catalysts for uneven natural reactions and, in a organic context, as anti-tumor brokers or biolabels.This booklet covers terpyridine-based fabrics subject matters starting from syntheses, chemistry, and multinuclear steel complexes, correct as much as functionalized polymers, 3D-architectures, and surfaces.The booklet is of curiosity for materials scientists, (in)organic chemists, polymer chemists, complicated chemists, actual chemists, biochemists, and libraries.
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Extra resources for Terpyridine-based Materials: For Catalytic, Optoelectronic and Life Science Applications
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7 (a) The X-shaped bis(terpyridine) 97. (b) The sensing experiments with 97 according to Brombosz et al. [175]: the top two rows show the emission color of 97 in an acetone–H2O mixture in the presence of various metal ions; the bottom row depicts the emission color of 97 (denoted as XF), the ZnII complex of 97 (denoted as XF Zn2 þ ), and the change in emission in the presence of various anions. Figure reproduced with kind permission; r 2007 American Chemical Society. homolog) are the first examples with pendant polypyridyl ligands and open the way for the marriage of the optoelectronic properties of the “superaromatic” HBC substituent with those of metal ion bis(terpyridine) complexes.
11). 5. The –NO2 moiety can be converted into –NH2 by reduction, for example, with hydrazine hydrate and palladium on charcoal, as catalyst [57]. Fallahpour et al. , BrÀ, IÀ) [2]. 11 4 -Nitro-functionalized terpyridines, as substrates for functional-groupinterconversion (“tpy” denotes any substituted 2,20 :60 ,200 -terpyridine motif) . , NaBH4 or SnCl2 Á 2H2O, as reductants) gave access to (E)-1,2-bis(terpyridin40 -yl)diazenes in moderate yields [130]. 3). With respect of applications, as reactant, in CuI-catalyzed alkyne-azide [2 þ 3]cycloaddition (CCAAC) reactions, 40 -azido-2,20 :60 ,200 -terpyridine (48) has recently gained considerable interest: the so-called “click reaction” enables the functionalization of terpyridine derivatives by reaction with terminal alkynes, yielding (1H1,2,3-triazol-1-yl)-substituted terpyridines 49.
02 27 J l 2011 15 38 24 | 31 32 | 2 Synthesis, Properties, and Applications of Functionalized 2,2 :6 ,2 -Terpyridines 0 0 00 N R' R N N N "cat. 18 Synthesis of Ziessel-type terpyridines 78 via Sonogashira cross-coupling reaction. [155]. 2. 19a by ethynylation of 62 with trimethylsilylacetylene or 2-methylbut-3-yn-2-ol under mild conditions and subsequent deprotection with KF or KOH, respectively [156, 157]. 19b) [158]. The authors proposed that such a stepwise oligomerization should be feasible until solubility and/or inertness of the intermediates constrains the reaction (as already observed in the second sequence in which 80 was converted into 81 in about 20% yield).