Synthetic pores with sticky π-clamps

Hiroyuki Tanaka; Guillaume Bollot; Jiri Mareda; Svetlana Litvinchuk; Duy-Hien Tran; Naomi Sakai; Stefan Matile

doi:10.1039/B702255G

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Organic & Biomolecular Chemistry

Issue 9, 2007

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Synthetic pores with sticky π-clamps

Hiroyuki Tanaka , Guillaume Bollot , Jiri Mareda , Svetlana Litvinchuk , Duy-Hien Tran , Naomi Sakai and Stefan Matile

Org. Biomol. Chem., 2007, 5, 1369-1380

DOI: 10.1039/B702255G
Received 12 Feb 2007, Accepted 19 Mar 2007
First published on the web 03 Apr 2007

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Abstract
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In this report, we describe design, synthesis, evaluation and molecular dynamics simulations of synthetic multifunctional pores with π-acidic naphthalenediimide clamps. Experimental evidence is provided for the formation of unstable but inert, heterogeneous and acid-insensitive dynamic tetrameric pores that are sensitive to base and ionic strength. Blockage experiments reveal that the introduction of aromatic electron donor–acceptor interactions provides access to the selective recognition of π-basic intercalators within the pore. This breakthrough is important for the application of synthetic pores as multianalyte sensors.

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Articles By

Hiroyuki Tanaka
Guillaume Bollot
Jiri Mareda
Svetlana Litvinchuk
Duy-Hien Tran
Naomi Sakai
Stefan Matile

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Organic & Biomolecular Chemistry

Synthetic pores with sticky π-clamps

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