A cyclic indole tetramer has been synthesized via an iridium-catalysed C–H borylation–cross coupling sequence. The tetraindole has a highly distorted structure, but can be oxidized with bromine and water into a highly planar macrocycle. The oxidized macrocycle can capture metal ions in its inner cavity as a novel porphyrin analogue, accompanied by a significant colour change from purple to blue or black.
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Nakamura et al. (2011) studied this question.
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