Synthesis and conformational studies of a series of 5,17-bis-aryl-25,26,27,28-tetrapropoxycalix[4]arenes: The influence of π-π interactions on the molecular structure

M. Larsen; Frederik C Krebs; N. Harrit; M. Jørgensen

doi:10.1039/a901881f

Synthesis and conformational studies of a series of 5,17-bis-aryl-25,26,27,28-tetrapropoxycalix[4]arenes: The influence of π-π interactions on the molecular structure

M. Larsen, Frederik C Krebs, N. Harrit, M. Jørgensen

Research output: Contribution to journal › Journal article › Research › peer-review

Abstract

Four 5,17-bis-aryl-25,26,27,28-tetrapropoxycalix[4]arenes were prepared via Negishi, Suzuki and Ullman type couplings [aryl = phenyl (1), 3-bromophenyl (2), 1-naphthyl (3) and carbazol-9-yl (4)]. The influence of the aryl groups on the structure was studied by X-ray crystallography, NMR, electronic absorption and fluorescence spectroscopy. The results show a drastic difference in conformation where 1 and 2 prefer to have the substituents away from each other while 3 and 4 have them in close contact. The photophysical properties of 3 and 4 exhibited a very solvent dependent fluorescence.

Original language	English
Journal	Royal Chemical Society. Journal. Perkin Transactions 2
Volume	2
Issue number	8
Pages (from-to)	1749-1757
ISSN	1472-779X
DOIs	https://doi.org/10.1039/a901881f
Publication status	Published - 1999

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title = "Synthesis and conformational studies of a series of 5,17-bis-aryl-25,26,27,28-tetrapropoxycalix[4]arenes: The influence of π-π interactions on the molecular structure",

abstract = "Four 5,17-bis-aryl-25,26,27,28-tetrapropoxycalix[4]arenes were prepared via Negishi, Suzuki and Ullman type couplings [aryl = phenyl (1), 3-bromophenyl (2), 1-naphthyl (3) and carbazol-9-yl (4)]. The influence of the aryl groups on the structure was studied by X-ray crystallography, NMR, electronic absorption and fluorescence spectroscopy. The results show a drastic difference in conformation where 1 and 2 prefer to have the substituents away from each other while 3 and 4 have them in close contact. The photophysical properties of 3 and 4 exhibited a very solvent dependent fluorescence.",

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author = "M. Larsen and Krebs, {Frederik C} and N. Harrit and M. J{\o}rgensen",

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doi = "10.1039/a901881f",

language = "English",

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journal = "Royal Chemical Society. Journal. Perkin Transactions 2",

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Synthesis and conformational studies of a series of 5,17-bis-aryl-25,26,27,28-tetrapropoxycalix[4]arenes: The influence of π-π interactions on the molecular structure. / Larsen, M.; Krebs, Frederik C; Harrit, N. et al.
In: Royal Chemical Society. Journal. Perkin Transactions 2, Vol. 2, No. 8, 1999, p. 1749-1757.

Research output: Contribution to journal › Journal article › Research › peer-review

TY - JOUR

T1 - Synthesis and conformational studies of a series of 5,17-bis-aryl-25,26,27,28-tetrapropoxycalix[4]arenes: The influence of π-π interactions on the molecular structure

AU - Larsen, M.

AU - Krebs, Frederik C

AU - Harrit, N.

AU - Jørgensen, M.

PY - 1999

Y1 - 1999

N2 - Four 5,17-bis-aryl-25,26,27,28-tetrapropoxycalix[4]arenes were prepared via Negishi, Suzuki and Ullman type couplings [aryl = phenyl (1), 3-bromophenyl (2), 1-naphthyl (3) and carbazol-9-yl (4)]. The influence of the aryl groups on the structure was studied by X-ray crystallography, NMR, electronic absorption and fluorescence spectroscopy. The results show a drastic difference in conformation where 1 and 2 prefer to have the substituents away from each other while 3 and 4 have them in close contact. The photophysical properties of 3 and 4 exhibited a very solvent dependent fluorescence.

AB - Four 5,17-bis-aryl-25,26,27,28-tetrapropoxycalix[4]arenes were prepared via Negishi, Suzuki and Ullman type couplings [aryl = phenyl (1), 3-bromophenyl (2), 1-naphthyl (3) and carbazol-9-yl (4)]. The influence of the aryl groups on the structure was studied by X-ray crystallography, NMR, electronic absorption and fluorescence spectroscopy. The results show a drastic difference in conformation where 1 and 2 prefer to have the substituents away from each other while 3 and 4 have them in close contact. The photophysical properties of 3 and 4 exhibited a very solvent dependent fluorescence.

KW - Nye funktionelle materialer

U2 - 10.1039/a901881f

DO - 10.1039/a901881f

M3 - Journal article

SN - 1472-779X

VL - 2

SP - 1749

EP - 1757

JO - Royal Chemical Society. Journal. Perkin Transactions 2

JF - Royal Chemical Society. Journal. Perkin Transactions 2

IS - 8

ER -

Synthesis and conformational studies of a series of 5,17-bis-aryl-25,26,27,28-tetrapropoxycalix[4]arenes: The influence of π-π interactions on the molecular structure

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