Facile Incorporation of Pd(PPh3)2Hal Substituents into Polymethines, Merocyanines, and Perylene Diimides as a Means of Suppressing Intermolecular Interactions

Compounds with polarizable π systems that are susceptible to attack with nucleophiles at C-Hal (Hal = Cl, Br) bonds react with Pd(PPh3)4 to yield net oxidative addition. X-ray structures show that the resulting Pd(PPh3)2Hal groups greatly reduce intermolecular π-π interactions. The Pd-functionalized dyes generally exhibit solution-like absorption spectra in films, whereas their Hal analogues exhibit features attributable to aggregation. © 2016 American Chemical Society.

Authors
Davydenko I.1 , Barlow S.1 , Sharma R.2 , Benis S.2 , Simon J.1 , Allen T.G.1 , Cooper M.W.1 , Khrustalev V. 3, 4 , Jucov E.V.3 , Castañeda R.3 , Ordonez C.3 , Li Z.5 , Chi S.-H.1 , Jang S.-H.5 , Parker T.C.1 , Timofeeva T.V.3 , Perry J.W.1 , Jen A.K.-Y.5 , Hagan D.J.2 , Van Stryland E.W. , Marder S.R.1
Journal
Journal of the American Chemical Society
Publisher
American Chemical Society
Number of issue
32
Language
English
Pages
10112-10115
Status
Published
Link
External link
DOI
10.1021/jacs.6b06361
Volume
138
Year
2016
Organizations
  • 1 School of Chemistry and Biochemistry, Center for Organic Photonics and Electronics, Georgia Institute of Technology, Atlanta, GA 30332-0400, United States
  • 2 CREOL, College of Optics and Photonics, University of Central Florida, Orlando, FL 32816, United States
  • 3 Department of Chemistry, New Mexico Highlands University, Las Vegas, NM 87701, United States
  • 4 Department of Inorganic Chemistry, Peoples' Friendship University of Russia, Moscow, 117198, Russian Federation
  • 5 Department of Materials Science and Engineering, University of Washington, Seattle, WA 98195, United States
Keywords
Bromine compounds; Chlorine compounds; Functionalized; Intermolecular interactions; Oxidative additions; Perylene diimides; Pi interactions; Pi systems; X-ray structure; Fighter aircraft; bromine; carbon; dye; merocyanine; nucleophile; palladium; perylene; perylene diimide; unclassified drug; absorption; Article; covalent bond; crystal structure; molecular interaction; quantum yield
Date of creation
19.10.2018
Date of change
19.10.2018
Short link
https://repository.rudn.ru/en/records/article/record/3852/
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