This lecture will discuss the use of templates for building large pi-conjugated macrocycles, and will show that it is possible to go beyond simple 1:1 template:product stoichiometries to direct the synthesis of very large nanorings using small templates. For example the Vernier principle enables the figure-of-eight complex shown below (Figure 1) to be prepared directly from a porphyrin tetramer. We have used this strategy to synthesize covalent nanorings consisting of up to 50 porphyrin units. These molecules are well into the size-range of proteins. They form complexes which display protein-like cooperative denaturation, and which mimic some aspects of the photophysical behavior of light-harvesting chlorophyll arrays.

Template-directed synthesis and supramolecular chemistry of porphyrin nanorings

247th National Meeting (2014)

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