Unusual molecular conformations in fluorinated, contorted hexabenzocoronenes

Yueh Lin Loo; Anna M. Hiszpanski; Bumjung Kim; Sujun Wei; Chien Yang Chiu; Michael L. Steigerwald; Colin Nuckolls

doi:10.1021/ol102016m

Unusual molecular conformations in fluorinated, contorted hexabenzocoronenes

Yueh Lin Loo, Anna M. Hiszpanski, Bumjung Kim, Sujun Wei, Chien Yang Chiu, Michael L. Steigerwald, Colin Nuckolls

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

42 Scopus citations

Abstract

Fluorinated, contorted hexabenzocoronenes (HBCs) have been synthesized in a facile manner via Suzuki-Miyaura coupling of fluorinated phenyl boronic acids followed by photocyclization and Scholl cyclization. In addition to the molecular conformation observed in previous HBC derivatives, close-contact fluorine-fluorine intramolecular interactions result in a metastable conformation not previously observed. Heating the metastable HBCs above 100 °C irreversibly converts them to the stable conformation, suggesting that the metastable conformation arises from a kinetically arrested state during cyclization.

Original language	English (US)
Pages (from-to)	4840-4843
Number of pages	4
Journal	Organic letters
Volume	12
Issue number	21
DOIs	https://doi.org/10.1021/ol102016m
State	Published - Nov 5 2010

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol102016m

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title = "Unusual molecular conformations in fluorinated, contorted hexabenzocoronenes",

abstract = "Fluorinated, contorted hexabenzocoronenes (HBCs) have been synthesized in a facile manner via Suzuki-Miyaura coupling of fluorinated phenyl boronic acids followed by photocyclization and Scholl cyclization. In addition to the molecular conformation observed in previous HBC derivatives, close-contact fluorine-fluorine intramolecular interactions result in a metastable conformation not previously observed. Heating the metastable HBCs above 100 °C irreversibly converts them to the stable conformation, suggesting that the metastable conformation arises from a kinetically arrested state during cyclization.",

author = "Loo, \{Yueh Lin\} and Hiszpanski, \{Anna M.\} and Bumjung Kim and Sujun Wei and Chiu, \{Chien Yang\} and Steigerwald, \{Michael L.\} and Colin Nuckolls",

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doi = "10.1021/ol102016m",

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T1 - Unusual molecular conformations in fluorinated, contorted hexabenzocoronenes

AU - Loo, Yueh Lin

AU - Hiszpanski, Anna M.

AU - Kim, Bumjung

AU - Wei, Sujun

AU - Chiu, Chien Yang

AU - Steigerwald, Michael L.

AU - Nuckolls, Colin

PY - 2010/11/5

Y1 - 2010/11/5

N2 - Fluorinated, contorted hexabenzocoronenes (HBCs) have been synthesized in a facile manner via Suzuki-Miyaura coupling of fluorinated phenyl boronic acids followed by photocyclization and Scholl cyclization. In addition to the molecular conformation observed in previous HBC derivatives, close-contact fluorine-fluorine intramolecular interactions result in a metastable conformation not previously observed. Heating the metastable HBCs above 100 °C irreversibly converts them to the stable conformation, suggesting that the metastable conformation arises from a kinetically arrested state during cyclization.

AB - Fluorinated, contorted hexabenzocoronenes (HBCs) have been synthesized in a facile manner via Suzuki-Miyaura coupling of fluorinated phenyl boronic acids followed by photocyclization and Scholl cyclization. In addition to the molecular conformation observed in previous HBC derivatives, close-contact fluorine-fluorine intramolecular interactions result in a metastable conformation not previously observed. Heating the metastable HBCs above 100 °C irreversibly converts them to the stable conformation, suggesting that the metastable conformation arises from a kinetically arrested state during cyclization.

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M3 - Article

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SN - 1523-7060

VL - 12

SP - 4840

EP - 4843

JO - Organic letters

JF - Organic letters

IS - 21

ER -

Unusual molecular conformations in fluorinated, contorted hexabenzocoronenes

Abstract

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