The synthesis of lactone-bridged 1,3,5-triphenylbenzene derivatives as pi-expanded coumarin triskelions

Heather A. Hintz; Nicholas J. Sortedahl; Samantha M. Meyer; Daniel A. Decato; Bart J. Dahl

doi:10.1016/j.tetlet.2017.11.010

The synthesis of lactone-bridged 1,3,5-triphenylbenzene derivatives as pi-expanded coumarin triskelions

Heather A. Hintz
, Nicholas J. Sortedahl
, Samantha M. Meyer
, Daniel A. Decato
, Bart J. Dahl

Chemistry and Biochemistry

University of Wisconsin-Eau Claire

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

11 Scopus citations

Abstract

Two triply lactone-bridged 1,3,5-triphenylbenzene derivatives with solubilizing moieties have been synthesized in five and six steps from commercially available starting materials. Compounds containing the 1,3,5-triphenylbenzene core with two atom bridges are relatively unknown. This new class of pi-expanded coumarins contain triskelion architectures and X-ray crystallographic studies of one of the triskelions indicates that the 1,3,5-triphenylbenzene core adopts a near-planar geometry. This is the only known example of a two atom-bridged 1,3,5-triphenylbenzene derivative to adopt a planar structure.

Original language	English
Pages (from-to)	4703-4708
Number of pages	6
Journal	Tetrahedron Letters
Volume	58
Issue number	50
DOIs	https://doi.org/10.1016/j.tetlet.2017.11.010
State	Published - Dec 13 2017

Keywords

Branched molecules
Coumarins
Extended conjugation
Planar geometry
Triskelions

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10.1016/j.tetlet.2017.11.010

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title = "The synthesis of lactone-bridged 1,3,5-triphenylbenzene derivatives as pi-expanded coumarin triskelions",

abstract = "Two triply lactone-bridged 1,3,5-triphenylbenzene derivatives with solubilizing moieties have been synthesized in five and six steps from commercially available starting materials. Compounds containing the 1,3,5-triphenylbenzene core with two atom bridges are relatively unknown. This new class of pi-expanded coumarins contain triskelion architectures and X-ray crystallographic studies of one of the triskelions indicates that the 1,3,5-triphenylbenzene core adopts a near-planar geometry. This is the only known example of a two atom-bridged 1,3,5-triphenylbenzene derivative to adopt a planar structure.",

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T1 - The synthesis of lactone-bridged 1,3,5-triphenylbenzene derivatives as pi-expanded coumarin triskelions

AU - Hintz, Heather A.

AU - Sortedahl, Nicholas J.

AU - Meyer, Samantha M.

AU - Decato, Daniel A.

AU - Dahl, Bart J.

PY - 2017/12/13

Y1 - 2017/12/13

N2 - Two triply lactone-bridged 1,3,5-triphenylbenzene derivatives with solubilizing moieties have been synthesized in five and six steps from commercially available starting materials. Compounds containing the 1,3,5-triphenylbenzene core with two atom bridges are relatively unknown. This new class of pi-expanded coumarins contain triskelion architectures and X-ray crystallographic studies of one of the triskelions indicates that the 1,3,5-triphenylbenzene core adopts a near-planar geometry. This is the only known example of a two atom-bridged 1,3,5-triphenylbenzene derivative to adopt a planar structure.

AB - Two triply lactone-bridged 1,3,5-triphenylbenzene derivatives with solubilizing moieties have been synthesized in five and six steps from commercially available starting materials. Compounds containing the 1,3,5-triphenylbenzene core with two atom bridges are relatively unknown. This new class of pi-expanded coumarins contain triskelion architectures and X-ray crystallographic studies of one of the triskelions indicates that the 1,3,5-triphenylbenzene core adopts a near-planar geometry. This is the only known example of a two atom-bridged 1,3,5-triphenylbenzene derivative to adopt a planar structure.

KW - Branched molecules

KW - Coumarins

KW - Extended conjugation

KW - Planar geometry

KW - Triskelions

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M3 - Article

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ER -

The synthesis of lactone-bridged 1,3,5-triphenylbenzene derivatives as pi-expanded coumarin triskelions

Abstract

Keywords

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