Bispyrrolotetrathiafulvalene-containing [2]catenanes

Michael R. Tomcsi; J. Fraser Stoddart

doi:10.1021/jo701374b

Bispyrrolotetrathiafulvalene-containing [2]catenanes

Michael R. Tomcsi, J. Fraser Stoddart^*

^*Corresponding author for this work

Chemistry

Research output: Contribution to journal › Article › peer-review

13 Scopus citations

Abstract

(Figure Presented) Two [2]catenanes incorporating bispyrrolotetrathiafulvalene (BPTTF) and weaker aryl donors, hydroquinone (HQ) and 1,5-dioxynaphthalene (DNP), respectively, have been prepared and characterized. These [2]catenanes show a predominant amount (>95:5) of the co-conformation in which either the HQ or the DNP unit is encircled by a tetracationic cyclophane, cyclobis(paraquat-p-phenylene) (CBPQT⁴⁺), contrary to what is observed in systems based on the parent tetrathiafulvalene (TTF). These new [2]catenanes act effectively as molecular switches which are always configured in the "on" state.

Original language	English (US)
Pages (from-to)	9335-9338
Number of pages	4
Journal	Journal of Organic Chemistry
Volume	72
Issue number	24
DOIs	https://doi.org/10.1021/jo701374b
State	Published - Nov 23 2007

ASJC Scopus subject areas

Organic Chemistry

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title = "Bispyrrolotetrathiafulvalene-containing [2]catenanes",

abstract = "(Figure Presented) Two [2]catenanes incorporating bispyrrolotetrathiafulvalene (BPTTF) and weaker aryl donors, hydroquinone (HQ) and 1,5-dioxynaphthalene (DNP), respectively, have been prepared and characterized. These [2]catenanes show a predominant amount (>95:5) of the co-conformation in which either the HQ or the DNP unit is encircled by a tetracationic cyclophane, cyclobis(paraquat-p-phenylene) (CBPQT4+), contrary to what is observed in systems based on the parent tetrathiafulvalene (TTF). These new [2]catenanes act effectively as molecular switches which are always configured in the {"}on{"} state.",

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N2 - (Figure Presented) Two [2]catenanes incorporating bispyrrolotetrathiafulvalene (BPTTF) and weaker aryl donors, hydroquinone (HQ) and 1,5-dioxynaphthalene (DNP), respectively, have been prepared and characterized. These [2]catenanes show a predominant amount (>95:5) of the co-conformation in which either the HQ or the DNP unit is encircled by a tetracationic cyclophane, cyclobis(paraquat-p-phenylene) (CBPQT4+), contrary to what is observed in systems based on the parent tetrathiafulvalene (TTF). These new [2]catenanes act effectively as molecular switches which are always configured in the "on" state.

AB - (Figure Presented) Two [2]catenanes incorporating bispyrrolotetrathiafulvalene (BPTTF) and weaker aryl donors, hydroquinone (HQ) and 1,5-dioxynaphthalene (DNP), respectively, have been prepared and characterized. These [2]catenanes show a predominant amount (>95:5) of the co-conformation in which either the HQ or the DNP unit is encircled by a tetracationic cyclophane, cyclobis(paraquat-p-phenylene) (CBPQT4+), contrary to what is observed in systems based on the parent tetrathiafulvalene (TTF). These new [2]catenanes act effectively as molecular switches which are always configured in the "on" state.

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