Synthesis and anion binding studies of o-phenylenevinylene-bridged tetrapyrrolic macrocycle as an expanded analogue of calix[4]pyrrole

Sudip Kumar Ghosh; Masatoshi Ishida; Jiazhu Li; Won Young Cha; Vincent M. Lynch; Dongho Kim; Jonathan L. Sessler

doi:10.1039/c4cc00686k

Synthesis and anion binding studies of o-phenylenevinylene-bridged tetrapyrrolic macrocycle as an expanded analogue of calix[4]pyrrole

Sudip Kumar Ghosh, Masatoshi Ishida, Jiazhu Li, Won Young Cha, Vincent M. Lynch, Dongho Kim, Jonathan L. Sessler

Applied Chemistry

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

12 Citations (Scopus)

Abstract

An o-phenylenevinylene-bridged tetrapyrrolic macrocycle (2) was synthesized by means of a Horner–Wadsworth–Emmons reaction between benzylbisphosphonate and SEM-protected diformylpyrrole, followed by deprotection of the SEM groups. This conformationally flexible tetrapyrrole can be considered as an expanded calix[4]pyrrole analogue, which acts as a receptor for the chloride and bromide anions in THF-d₈, but undergoes deprotonation upon exposure to the fluoride anion.

Original language	English
Pages (from-to)	3753-3756
Number of pages	4
Journal	Chemical Communications
Volume	50
Issue number	28
DOIs	https://doi.org/10.1039/c4cc00686k
Publication status	Published - Mar 11 2014

All Science Journal Classification (ASJC) codes

Catalysis
Electronic, Optical and Magnetic Materials
Ceramics and Composites
Chemistry(all)
Surfaces, Coatings and Films
Metals and Alloys
Materials Chemistry

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abstract = "An o-phenylenevinylene-bridged tetrapyrrolic macrocycle (2) was synthesized by means of a Horner–Wadsworth–Emmons reaction between benzylbisphosphonate and SEM-protected diformylpyrrole, followed by deprotection of the SEM groups. This conformationally flexible tetrapyrrole can be considered as an expanded calix[4]pyrrole analogue, which acts as a receptor for the chloride and bromide anions in THF-d8, but undergoes deprotonation upon exposure to the fluoride anion.",

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AU - Ghosh, Sudip Kumar

AU - Ishida, Masatoshi

AU - Li, Jiazhu

AU - Cha, Won Young

AU - Lynch, Vincent M.

AU - Kim, Dongho

AU - Sessler, Jonathan L.

PY - 2014/3/11

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N2 - An o-phenylenevinylene-bridged tetrapyrrolic macrocycle (2) was synthesized by means of a Horner–Wadsworth–Emmons reaction between benzylbisphosphonate and SEM-protected diformylpyrrole, followed by deprotection of the SEM groups. This conformationally flexible tetrapyrrole can be considered as an expanded calix[4]pyrrole analogue, which acts as a receptor for the chloride and bromide anions in THF-d8, but undergoes deprotonation upon exposure to the fluoride anion.

AB - An o-phenylenevinylene-bridged tetrapyrrolic macrocycle (2) was synthesized by means of a Horner–Wadsworth–Emmons reaction between benzylbisphosphonate and SEM-protected diformylpyrrole, followed by deprotection of the SEM groups. This conformationally flexible tetrapyrrole can be considered as an expanded calix[4]pyrrole analogue, which acts as a receptor for the chloride and bromide anions in THF-d8, but undergoes deprotonation upon exposure to the fluoride anion.

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Synthesis and anion binding studies of o-phenylenevinylene-bridged tetrapyrrolic macrocycle as an expanded analogue of calix[4]pyrrole

Abstract

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