Tweezer-type binding cavity formed by the helical folding of a carbazole-pyridine oligomer

Hye Jin Jang; Seungwon Lee; Byung Jun An; Geunmoo Song; Hae Geun Jeon; Kyu Sung Jeong

doi:10.1039/d1cc06569f

Tweezer-type binding cavity formed by the helical folding of a carbazole-pyridine oligomer

Hye Jin Jang, Seungwon Lee, Byung Jun An, Geunmoo Song, Hae Geun Jeon, Kyu Sung Jeong

Department of Chemistry

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

1 Citation (Scopus)

Abstract

We have synthesised a new aromatic foldamer based on the carbazole-pyridine oligomers that adopt helical conformations via dipole-dipole interactions and π-stacking between two ethynyl bond-linked monomers. This foldamer scaffold has been further modified into a synthetic receptor with a tweezer-type binding cavity outside the helical backbone upon folding, in contrast to most aromatic foldamers with internal binding cavities. The tweezer-type cavity is composed of two parallel pyrenyl planes, allowing for the intercalation of a naphthalenediimide guest via π-stacking and CH⋯O interactions, as demonstrated using its 1H NMR spectra and X-ray crystal structure.

Original language	English
Pages (from-to)	1410-1413
Number of pages	4
Journal	Chemical Communications
Volume	58
Issue number	9
DOIs	https://doi.org/10.1039/d1cc06569f
Publication status	Published - 2022 Jan 28

Bibliographical note

Funding Information:
This study was supported by a grant from the National Research Foundation of Korea (NRF), which was funded by the Korean government ((MSIT) 2021R1A2C109359111). The authors thank the Pohang Accelerator Laboratory (PAL) for beamline time (2018-1st-2D-012, 2021-3rd-2D-029).

Publisher Copyright:
© The Royal Society of Chemistry.

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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title = "Tweezer-type binding cavity formed by the helical folding of a carbazole-pyridine oligomer",

abstract = "We have synthesised a new aromatic foldamer based on the carbazole-pyridine oligomers that adopt helical conformations via dipole-dipole interactions and π-stacking between two ethynyl bond-linked monomers. This foldamer scaffold has been further modified into a synthetic receptor with a tweezer-type binding cavity outside the helical backbone upon folding, in contrast to most aromatic foldamers with internal binding cavities. The tweezer-type cavity is composed of two parallel pyrenyl planes, allowing for the intercalation of a naphthalenediimide guest via π-stacking and CH⋯O interactions, as demonstrated using its 1H NMR spectra and X-ray crystal structure.",

author = "Jang, {Hye Jin} and Seungwon Lee and An, {Byung Jun} and Geunmoo Song and Jeon, {Hae Geun} and Jeong, {Kyu Sung}",

note = "Funding Information: This study was supported by a grant from the National Research Foundation of Korea (NRF), which was funded by the Korean government ((MSIT) 2021R1A2C109359111). The authors thank the Pohang Accelerator Laboratory (PAL) for beamline time (2018-1st-2D-012, 2021-3rd-2D-029). Publisher Copyright: {\textcopyright} The Royal Society of Chemistry.",

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T1 - Tweezer-type binding cavity formed by the helical folding of a carbazole-pyridine oligomer

AU - Jang, Hye Jin

AU - Lee, Seungwon

AU - An, Byung Jun

AU - Song, Geunmoo

AU - Jeon, Hae Geun

AU - Jeong, Kyu Sung

N1 - Funding Information: This study was supported by a grant from the National Research Foundation of Korea (NRF), which was funded by the Korean government ((MSIT) 2021R1A2C109359111). The authors thank the Pohang Accelerator Laboratory (PAL) for beamline time (2018-1st-2D-012, 2021-3rd-2D-029). Publisher Copyright: © The Royal Society of Chemistry.

PY - 2022/1/28

Y1 - 2022/1/28

N2 - We have synthesised a new aromatic foldamer based on the carbazole-pyridine oligomers that adopt helical conformations via dipole-dipole interactions and π-stacking between two ethynyl bond-linked monomers. This foldamer scaffold has been further modified into a synthetic receptor with a tweezer-type binding cavity outside the helical backbone upon folding, in contrast to most aromatic foldamers with internal binding cavities. The tweezer-type cavity is composed of two parallel pyrenyl planes, allowing for the intercalation of a naphthalenediimide guest via π-stacking and CH⋯O interactions, as demonstrated using its 1H NMR spectra and X-ray crystal structure.

AB - We have synthesised a new aromatic foldamer based on the carbazole-pyridine oligomers that adopt helical conformations via dipole-dipole interactions and π-stacking between two ethynyl bond-linked monomers. This foldamer scaffold has been further modified into a synthetic receptor with a tweezer-type binding cavity outside the helical backbone upon folding, in contrast to most aromatic foldamers with internal binding cavities. The tweezer-type cavity is composed of two parallel pyrenyl planes, allowing for the intercalation of a naphthalenediimide guest via π-stacking and CH⋯O interactions, as demonstrated using its 1H NMR spectra and X-ray crystal structure.

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EP - 1413

JO - Chemical Communications

JF - Chemical Communications

IS - 9

ER -

Tweezer-type binding cavity formed by the helical folding of a carbazole-pyridine oligomer

Abstract

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