New NLO stilbene derivatives bearing phosphonate ester electron-withdrawing groups

Kevin D. Belfield; Chandrasekhar Chinna; Katherine J. Schafer

doi:10.1016/S0040-4039(97)01390-7

New NLO stilbene derivatives bearing phosphonate ester electron-withdrawing groups

Kevin D. Belfield, Chandrasekhar Chinna, Katherine J. Schafer

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

34 Scopus citations

Abstract

The synthesis and characterization of a new class of electron donor-acceptor substituted stilbenes hearing a phosphonate ester as the electron-withdrawing functionality is described. Phosphorylation of aromatic rings was accomplished using Ni-catalyzed Arbuzov reactions, while Pd-catalyzed Heck-type coupling reactions were employed to construct the stilbene derivatives. Through determination of an electro-optic coefficient (r33), it was demonstrated that the phosphonate ester group is effective as an electron-withdrawing group for stilbene-based second-order NLO materials.

Original language	English (US)
Pages (from-to)	6131-6134
Number of pages	4
Journal	Tetrahedron Letters
Volume	38
Issue number	35
DOIs	https://doi.org/10.1016/S0040-4039(97)01390-7
State	Published - Sep 1 1997
Externally published	Yes

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4039(97)01390-7

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@article{950e8a4561154702a5c71cf4d73d90fb,

title = "New NLO stilbene derivatives bearing phosphonate ester electron-withdrawing groups",

abstract = "The synthesis and characterization of a new class of electron donor-acceptor substituted stilbenes hearing a phosphonate ester as the electron-withdrawing functionality is described. Phosphorylation of aromatic rings was accomplished using Ni-catalyzed Arbuzov reactions, while Pd-catalyzed Heck-type coupling reactions were employed to construct the stilbene derivatives. Through determination of an electro-optic coefficient (r33), it was demonstrated that the phosphonate ester group is effective as an electron-withdrawing group for stilbene-based second-order NLO materials.",

author = "Belfield, {Kevin D.} and Chandrasekhar Chinna and Schafer, {Katherine J.}",

note = "Funding Information: Financial support from the University of Detroit Mercy, College of Engineering and Science Research Initiation Program is acknowledged. The authors gratefully acknowledge Dr. Andrew Tyler of Harvard University for MS analyses and Dr. Richard Vaia of the USAF Wright Laboratories for electro-optic characterization. The Harvard University Department of Chemistry and Chemical Biology Mass Spectrometry Facility is supported by grants from NSF (CHE-900043) and NIH (SIO-RR06716). ",

year = "1997",

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doi = "10.1016/S0040-4039(97)01390-7",

language = "English (US)",

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pages = "6131--6134",

journal = "Tetrahedron Letters",

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T1 - New NLO stilbene derivatives bearing phosphonate ester electron-withdrawing groups

AU - Belfield, Kevin D.

AU - Chinna, Chandrasekhar

AU - Schafer, Katherine J.

N1 - Funding Information: Financial support from the University of Detroit Mercy, College of Engineering and Science Research Initiation Program is acknowledged. The authors gratefully acknowledge Dr. Andrew Tyler of Harvard University for MS analyses and Dr. Richard Vaia of the USAF Wright Laboratories for electro-optic characterization. The Harvard University Department of Chemistry and Chemical Biology Mass Spectrometry Facility is supported by grants from NSF (CHE-900043) and NIH (SIO-RR06716).

PY - 1997/9/1

Y1 - 1997/9/1

N2 - The synthesis and characterization of a new class of electron donor-acceptor substituted stilbenes hearing a phosphonate ester as the electron-withdrawing functionality is described. Phosphorylation of aromatic rings was accomplished using Ni-catalyzed Arbuzov reactions, while Pd-catalyzed Heck-type coupling reactions were employed to construct the stilbene derivatives. Through determination of an electro-optic coefficient (r33), it was demonstrated that the phosphonate ester group is effective as an electron-withdrawing group for stilbene-based second-order NLO materials.

AB - The synthesis and characterization of a new class of electron donor-acceptor substituted stilbenes hearing a phosphonate ester as the electron-withdrawing functionality is described. Phosphorylation of aromatic rings was accomplished using Ni-catalyzed Arbuzov reactions, while Pd-catalyzed Heck-type coupling reactions were employed to construct the stilbene derivatives. Through determination of an electro-optic coefficient (r33), it was demonstrated that the phosphonate ester group is effective as an electron-withdrawing group for stilbene-based second-order NLO materials.

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U2 - 10.1016/S0040-4039(97)01390-7

DO - 10.1016/S0040-4039(97)01390-7

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SP - 6131

EP - 6134

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 35

ER -

New NLO stilbene derivatives bearing phosphonate ester electron-withdrawing groups

Abstract

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