Compounds with polarizable pi 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)(2)Hal groups greatly reduce intermolecular interactions. The Pd-functionalited dyes generally exhibit solution-like absorption spectra in films, whereas their Hal analogues exhibit features attributable to aggregation.

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polarizable pi aggregation intermolecular pdpph32hal oxidative solutionlike absorption spectra pdfunctionalited dyes

Castaneda, R ,Benis, S ,Timofeeva, TV ,Sharma, R ,Ordonez, C ,Marder, SR,Davydenko, I ,Cooper, MW ,Chi, SH ,Hagan, DJ ,Khrustalev, V ,Perry, JW ,Li, ZA ,Allen, TG ,Barlow, S ,Jucov, EV ,Jang, SH ,Van Stryland, EW ,Jen, AKY ,Simon, J ,Parker, TC ,.Facile Incorporation of Pd(PPh3)(2)Hal Substituents into Polymethines, Merocyanines, and Perylene Diimides as a Means of Suppressing Intermolecular Interactions. 138 (),4.

Castaneda, R , et al."Facile Incorporation of Pd(PPh3)(2)Hal Substituents into Polymethines, Merocyanines, and Perylene Diimides as a Means of Suppressing Intermolecular Interactions" 138

Castaneda, R ,Benis, S ,Timofeeva, TV ,Sharma, R ,Ordonez, C ,Marder, SR,Davydenko, I ,Cooper, MW ,Chi, SH ,Hagan, DJ ,Khrustalev, V ,Perry, JW ,Li, ZA ,Allen, TG ,Barlow, S ,Jucov, EV ,Jang, SH ,Van Stryland, EW ,Jen, AKY ,Simon, J ,Parker, TC ,"Facile Incorporation of Pd(PPh3)(2)Hal Substituents into Polymethines, Merocyanines, and Perylene Diimides as a Means of Suppressing Intermolecular Interactions"