Semi-fused hexaphenyl hexa-peri-hexabenzocoronene: a novel fluorophore from an intramolecular Scholl reaction

Yunyi Lu; Jeffrey S. Moore

doi:10.1016/j.tetlet.2009.04.103

Semi-fused hexaphenyl hexa-peri-hexabenzocoronene: a novel fluorophore from an intramolecular Scholl reaction

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Abstract

A semi-fused hexaphenyl hexabenzocoronene derivative (hexaphenyl-1/2HBC) was discovered and isolated from an intramolecular Scholl reaction of an oligo(ethyleneglycol) substituted hexabiphenylbenzene. This new derivative exhibits blue-shifted λ_em and significantly enhanced fluorescence in dichloromethane compared to the completely cyclized hexaphenyl-HBC derivative.

Original language	English (US)
Pages (from-to)	4071-4077
Number of pages	7
Journal	Tetrahedron Letters
Volume	50
Issue number	28
DOIs	https://doi.org/10.1016/j.tetlet.2009.04.103
State	Published - Jul 15 2009

Keywords

Dehydrogenation
Fluorophore
Polycyclic aromatic hydrocarbons
Scholl condensation

ASJC Scopus subject areas

Biochemistry
Organic Chemistry
Drug Discovery

Online availability

10.1016/j.tetlet.2009.04.103

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title = "Semi-fused hexaphenyl hexa-peri-hexabenzocoronene: a novel fluorophore from an intramolecular Scholl reaction",

abstract = "A semi-fused hexaphenyl hexabenzocoronene derivative (hexaphenyl-1/2HBC) was discovered and isolated from an intramolecular Scholl reaction of an oligo(ethyleneglycol) substituted hexabiphenylbenzene. This new derivative exhibits blue-shifted λem and significantly enhanced fluorescence in dichloromethane compared to the completely cyclized hexaphenyl-HBC derivative.",

keywords = "Dehydrogenation, Fluorophore, Polycyclic aromatic hydrocarbons, Scholl condensation",

author = "Yunyi Lu and Moore, {Jeffrey S.}",

note = "Funding Information: This work was supported by the National Science Foundation Science (CHE-0642413) and the NSF Science Technology Center of Advanced Materials for the Purification of Water with Systems (WaterCAMPWS) (Grant No. CTS-0120978). We thank Furong Sun from the Mass Spectrometry Laboratory, SCS, University of Illinois for valuable expertise in ESI and MALDI-MS characterization experiments. Y.L. thanks Dr. Mitch Schultz for helpful discussions. ",

year = "2009",

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doi = "10.1016/j.tetlet.2009.04.103",

language = "English (US)",

volume = "50",

pages = "4071--4077",

journal = "Tetrahedron Letters",

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T1 - Semi-fused hexaphenyl hexa-peri-hexabenzocoronene

T2 - a novel fluorophore from an intramolecular Scholl reaction

AU - Lu, Yunyi

AU - Moore, Jeffrey S.

N1 - Funding Information: This work was supported by the National Science Foundation Science (CHE-0642413) and the NSF Science Technology Center of Advanced Materials for the Purification of Water with Systems (WaterCAMPWS) (Grant No. CTS-0120978). We thank Furong Sun from the Mass Spectrometry Laboratory, SCS, University of Illinois for valuable expertise in ESI and MALDI-MS characterization experiments. Y.L. thanks Dr. Mitch Schultz for helpful discussions.

PY - 2009/7/15

Y1 - 2009/7/15

N2 - A semi-fused hexaphenyl hexabenzocoronene derivative (hexaphenyl-1/2HBC) was discovered and isolated from an intramolecular Scholl reaction of an oligo(ethyleneglycol) substituted hexabiphenylbenzene. This new derivative exhibits blue-shifted λem and significantly enhanced fluorescence in dichloromethane compared to the completely cyclized hexaphenyl-HBC derivative.

AB - A semi-fused hexaphenyl hexabenzocoronene derivative (hexaphenyl-1/2HBC) was discovered and isolated from an intramolecular Scholl reaction of an oligo(ethyleneglycol) substituted hexabiphenylbenzene. This new derivative exhibits blue-shifted λem and significantly enhanced fluorescence in dichloromethane compared to the completely cyclized hexaphenyl-HBC derivative.

KW - Dehydrogenation

KW - Fluorophore

KW - Polycyclic aromatic hydrocarbons

KW - Scholl condensation

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DO - 10.1016/j.tetlet.2009.04.103

M3 - Article

AN - SCOPUS:66049108394

VL - 50

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EP - 4077

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 28

ER -

Semi-fused hexaphenyl hexa-peri-hexabenzocoronene: a novel fluorophore from an intramolecular Scholl reaction

Abstract

Keywords

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