Issue 11, 2015

Self-complementary double-stranded porphyrin arrays assembled from an alternating pyridyl–porphyrin sequence

Abstract

Oligomeric porphyrin arrays with an alternating pyridyl–porphyrin sequence were synthesized to explore double-strand formation through self-complementary pyridyl-to-zinc axial coordination bonds. Competitive titration experiments revealed the thermodynamic aspects involved in the zipper effect within double-strand formation. Multiple axial coordination bonds defined the stacked conformation, despite a marginal contribution to the stability of the double-strands. Thus, the zipper cooperativity was the dominant factor for the remarkable stability. Moreover, the dimeric and trimeric porphyrin arrays were independently assembled into double-strands by self-sorting from a binary mixture. Double-strand formation engineered discretely stacked π-systems. Successive slipped-cofacial stacks of the porphyrin rings progressively extended the π-system via exciton coupling over the double-strand while keeping a relatively high fluorescence quantum yield.

Graphical abstract: Self-complementary double-stranded porphyrin arrays assembled from an alternating pyridyl–porphyrin sequence

Supplementary files

Article information

Article type
Edge Article
Submitted
27 Mar 2015
Accepted
05 Aug 2015
First published
05 Aug 2015
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2015,6, 6199-6206

Author version available

Self-complementary double-stranded porphyrin arrays assembled from an alternating pyridyl–porphyrin sequence

M. Morisue, Y. Hoshino, K. Shimizu, M. Shimizu and Y. Kuroda, Chem. Sci., 2015, 6, 6199 DOI: 10.1039/C5SC01101A

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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