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Facile Incorporation of Pd(PPh3)2Hal Substituents into Polymethines, Merocyanines, and Perylene Diimides as a Means of Suppressing Intermolecular Interactions.
Davydenko, Iryna; Barlow, Stephen; Sharma, Rajesh; Benis, Sepehr; Simon, Janos; Allen, Taylor G; Cooper, Matthew W; Khrustalev, Victor; Jucov, Evgheni V; Castañeda, Raúl; Ordonez, Carlos; Li, Zhong'an; Chi, San-Hui; Jang, Sei-Hum; Parker, Timothy C; Timofeeva, Tatiana V; Perry, Joseph W; Jen, Alex K-Y; Hagan, David J; Van Stryland, Eric W; Marder, Seth R.
Affiliation
  • Davydenko I; School of Chemistry and Biochemistry and Center for Organic Photonics and Electronics, Georgia Institute of Technology , Atlanta, Georgia 30332-0400, United States.
  • Barlow S; School of Chemistry and Biochemistry and Center for Organic Photonics and Electronics, Georgia Institute of Technology , Atlanta, Georgia 30332-0400, United States.
  • Sharma R; CREOL, The College of Optics and Photonics, University of Central Florida , Orlando, Florida 32816, United States.
  • Benis S; CREOL, The College of Optics and Photonics, University of Central Florida , Orlando, Florida 32816, United States.
  • Simon J; School of Chemistry and Biochemistry and Center for Organic Photonics and Electronics, Georgia Institute of Technology , Atlanta, Georgia 30332-0400, United States.
  • Allen TG; School of Chemistry and Biochemistry and Center for Organic Photonics and Electronics, Georgia Institute of Technology , Atlanta, Georgia 30332-0400, United States.
  • Cooper MW; School of Chemistry and Biochemistry and Center for Organic Photonics and Electronics, Georgia Institute of Technology , Atlanta, Georgia 30332-0400, United States.
  • Khrustalev V; Department of Chemistry, New Mexico Highlands University , Las Vegas, New Mexico 87701, United States.
  • Jucov EV; Department of Inorganic Chemistry, Peoples' Friendship University of Russia , Moscow 117198, Russia.
  • Castañeda R; Department of Chemistry, New Mexico Highlands University , Las Vegas, New Mexico 87701, United States.
  • Ordonez C; Department of Chemistry, New Mexico Highlands University , Las Vegas, New Mexico 87701, United States.
  • Li Z; Department of Chemistry, New Mexico Highlands University , Las Vegas, New Mexico 87701, United States.
  • Chi SH; Department of Materials Science and Engineering, University of Washington , Seattle, Washington 98195, United States.
  • Jang SH; School of Chemistry and Biochemistry and Center for Organic Photonics and Electronics, Georgia Institute of Technology , Atlanta, Georgia 30332-0400, United States.
  • Parker TC; Department of Materials Science and Engineering, University of Washington , Seattle, Washington 98195, United States.
  • Timofeeva TV; School of Chemistry and Biochemistry and Center for Organic Photonics and Electronics, Georgia Institute of Technology , Atlanta, Georgia 30332-0400, United States.
  • Perry JW; Department of Chemistry, New Mexico Highlands University , Las Vegas, New Mexico 87701, United States.
  • Jen AK; School of Chemistry and Biochemistry and Center for Organic Photonics and Electronics, Georgia Institute of Technology , Atlanta, Georgia 30332-0400, United States.
  • Hagan DJ; Department of Materials Science and Engineering, University of Washington , Seattle, Washington 98195, United States.
  • Van Stryland EW; CREOL, The College of Optics and Photonics, University of Central Florida , Orlando, Florida 32816, United States.
  • Marder SR; CREOL, The College of Optics and Photonics, University of Central Florida , Orlando, Florida 32816, United States.
J Am Chem Soc ; 138(32): 10112-5, 2016 08 17.
Article in En | MEDLINE | ID: mdl-27494823
ABSTRACT
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.

Full text: 1 Database: MEDLINE Language: En Journal: J Am Chem Soc Year: 2016 Type: Article Affiliation country: United States

Full text: 1 Database: MEDLINE Language: En Journal: J Am Chem Soc Year: 2016 Type: Article Affiliation country: United States