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.; W. Van Stryland, Eric; Marder, Seth R.

doi:10.1021/jacs.6b06361.s001

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

journal contribution

posted on 2016-08-05, 17:03 authored by Iryna Davydenko, Stephen Barlow, Rajesh Sharma, Sepehr Benis, Janos Simon, Taylor G. Allen, Matthew W. Cooper, Victor Khrustalev, Evgheni V. Jucov, Raúl Castañeda, Carlos Ordonez, Zhong’an Li, San-Hui Chi, Sei-Hum Jang, Timothy C. Parker, Tatiana V. Timofeeva, Joseph W. Perry, Alex K.-Y. Jen, David J. Hagan, Eric W. Van Stryland, Seth R. Marder

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.