Homochiral self-sorted and emissive IrIII metallo-cryptophanes

Victoria E. Pritchard; Diego Rota Martir; Samuel Oldknow; Shumpei Kai; Shuichi Hiraoka; Nikki J. Cookson; Eli Zysman-Colman; Michaele J. Hardie

doi:10.1002/chem.201701348

Homochiral self-sorted and emissive Ir^III metallo-cryptophanes

Victoria E. Pritchard, Diego Rota Martir, Samuel Oldknow, Shumpei Kai, Shuichi Hiraoka, Nikki J. Cookson, Eli Zysman-Colman, Michaele J. Hardie

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

Abstract

The racemic ligands (±)-tris(isonicotinoyl)-cyclotriguaiacylene (L1), or (±)-tris(4-pyridyl-methyl)-cyclotriguaiacylene (L2) assemblewith racemic (Λ, Δ)- [Ir(ppy)₂(MeCN)₂]⁺, in which ppy = 2-phenylpyridinato to form [{Ir(ppy)₂}₃(L)₂]³⁺ metallo-cryptophane cages. The crystal structure of [{Ir(ppy)₂}₃(L1)₂]∙3BF₄ has MM-ΛΛΛ nd PP-ΔΔΔ isomers, and homochiral self-sorting occurs in solution, a processaccelerated by a chiral guest. Self-recognition between L1 and L2 within cagesdoes not occur, and cages show very slow ligand-exchange. Both cages are phosphorescent,with [{Ir(ppy)₂}₃(L2)₂]³⁺ havingenhanced and blue-shifted emission when compared with [{Ir(ppy)₂}₃(L1)₂]³⁺ .

Original language	English
Pages (from-to)	6290-6294
Journal	Chemistry - A European Journal
Volume	23
Issue number	26
Early online date	20 Apr 2017
DOIs	https://doi.org/10.1002/chem.201701348
Publication status	Published - 5 May 2017

Keywords

Supramolecular chemistry
Cage compounds
Homochiral self-sorting
Phosphorescence
Iridium

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© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim. This work has been made available online in accordance with the publisher’s policies. This is the author created, accepted version manuscript following peer review and may differ slightly from the final published version. The final published version of this work is available at: https://doi.org/10.1002/chem.201701348
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Cite this

@article{a0f63de3962842edb482c676ef0dad23,

title = "Homochiral self-sorted and emissive IrIII metallo-cryptophanes",

abstract = "The racemic ligands (±)-tris(isonicotinoyl)-cyclotriguaiacylene (L1), or (±)-tris(4-pyridyl-methyl)-cyclotriguaiacylene (L2) assemblewith racemic (Λ, Δ)- [Ir(ppy)2(MeCN)2]+, in which ppy = 2-phenylpyridinato to form [\{Ir(ppy)2\}3(L)2]3+ metallo-cryptophane cages. The crystal structure of [\{Ir(ppy)2\}3(L1)2]∙3BF4 has MM-ΛΛΛ nd PP-ΔΔΔ isomers, and homochiral self-sorting occurs in solution, a processaccelerated by a chiral guest. Self-recognition between L1 and L2 within cagesdoes not occur, and cages show very slow ligand-exchange. Both cages are phosphorescent,with [\{Ir(ppy)2\}3(L2)2]3+ havingenhanced and blue-shifted emission when compared with [\{Ir(ppy)2\}3(L1)2]3+ . ",

keywords = "Supramolecular chemistry, Cage compounds, Homochiral self-sorting, Phosphorescence, Iridium",

author = "Pritchard, \{Victoria E.\} and \{Rota Martir\}, Diego and Samuel Oldknow and Shumpei Kai and Shuichi Hiraoka and Cookson, \{Nikki J.\} and Eli Zysman-Colman and Hardie, \{Michaele J.\}",

note = "We thank the EPSRC (DTG award 1238852, EP/K039202/1, EP/M02105X/1, EP/J001325/1), Leverhulme Trust (RPG-2014-148), University of St Andrews, and the MEXT/JSPS Grants in Aid for Scientific Research (JP25102005 and JP25102001) for funding; Simon Barrett for assistance with NMR; Martin Huscroft for assistance with HPLC, and Stephen Boyer for elemental analysis measurements.",

year = "2017",

month = may,

day = "5",

doi = "10.1002/chem.201701348",

language = "English",

volume = "23",

pages = "6290--6294",

journal = "Chemistry - A European Journal",

issn = "0947-6539",

publisher = "John Wiley \& Sons, Ltd",

number = "26",

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T1 - Homochiral self-sorted and emissive IrIII metallo-cryptophanes

AU - Pritchard, Victoria E.

AU - Rota Martir, Diego

AU - Oldknow, Samuel

AU - Kai, Shumpei

AU - Hiraoka, Shuichi

AU - Cookson, Nikki J.

AU - Zysman-Colman, Eli

AU - Hardie, Michaele J.

N1 - We thank the EPSRC (DTG award 1238852, EP/K039202/1, EP/M02105X/1, EP/J001325/1), Leverhulme Trust (RPG-2014-148), University of St Andrews, and the MEXT/JSPS Grants in Aid for Scientific Research (JP25102005 and JP25102001) for funding; Simon Barrett for assistance with NMR; Martin Huscroft for assistance with HPLC, and Stephen Boyer for elemental analysis measurements.

PY - 2017/5/5

Y1 - 2017/5/5

N2 - The racemic ligands (±)-tris(isonicotinoyl)-cyclotriguaiacylene (L1), or (±)-tris(4-pyridyl-methyl)-cyclotriguaiacylene (L2) assemblewith racemic (Λ, Δ)- [Ir(ppy)2(MeCN)2]+, in which ppy = 2-phenylpyridinato to form [{Ir(ppy)2}3(L)2]3+ metallo-cryptophane cages. The crystal structure of [{Ir(ppy)2}3(L1)2]∙3BF4 has MM-ΛΛΛ nd PP-ΔΔΔ isomers, and homochiral self-sorting occurs in solution, a processaccelerated by a chiral guest. Self-recognition between L1 and L2 within cagesdoes not occur, and cages show very slow ligand-exchange. Both cages are phosphorescent,with [{Ir(ppy)2}3(L2)2]3+ havingenhanced and blue-shifted emission when compared with [{Ir(ppy)2}3(L1)2]3+ .

AB - The racemic ligands (±)-tris(isonicotinoyl)-cyclotriguaiacylene (L1), or (±)-tris(4-pyridyl-methyl)-cyclotriguaiacylene (L2) assemblewith racemic (Λ, Δ)- [Ir(ppy)2(MeCN)2]+, in which ppy = 2-phenylpyridinato to form [{Ir(ppy)2}3(L)2]3+ metallo-cryptophane cages. The crystal structure of [{Ir(ppy)2}3(L1)2]∙3BF4 has MM-ΛΛΛ nd PP-ΔΔΔ isomers, and homochiral self-sorting occurs in solution, a processaccelerated by a chiral guest. Self-recognition between L1 and L2 within cagesdoes not occur, and cages show very slow ligand-exchange. Both cages are phosphorescent,with [{Ir(ppy)2}3(L2)2]3+ havingenhanced and blue-shifted emission when compared with [{Ir(ppy)2}3(L1)2]3+ .

KW - Supramolecular chemistry

KW - Cage compounds

KW - Homochiral self-sorting

KW - Phosphorescence

KW - Iridium

UR - https://www.scopus.com/pages/publications/85018630010

U2 - 10.1002/chem.201701348

DO - 10.1002/chem.201701348

M3 - Article

SN - 0947-6539

VL - 23

SP - 6290

EP - 6294

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

IS - 26

ER -

Homochiral self-sorted and emissive Ir^III metallo-cryptophanes

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Keywords

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