3 years ago

Tunable Heck–Mizoroki Reaction of Dibromonaphthalene Diimide with Aryl Ethylenes: Design, Synthesis, and Characterization of Coplanar NDI-Based Conjugated Molecules

Tunable Heck–Mizoroki Reaction of Dibromonaphthalene Diimide with Aryl Ethylenes: Design, Synthesis, and Characterization of Coplanar NDI-Based Conjugated Molecules
Liang Cheng, Yangxiong Li, Chunling Gu, Dong Wang, Hongbing Fu, Lu Xiao, Li Liu
Rational design of coplanar NDI-based conjugated molecules was achieved by covalently connecting naphthalene diimide (NDI) units with aryl (Ar) groups through vinylene (V) linkers via Heck–Mizoroki reaction. Two series of products, diolefination products (ArVNDIVAr) and hydroxylated and mono-olefination products (HONDIVAr), can be obtained, respectively, in moderate to excellent yields (45–90%) under controlled conditions, in which catalyst and base play the key roles. Density functional theory calculation discloses the outstanding planarity of the two types of products. Large bathochromic shifts are observed in both the absorbance and photoluminescence spectra of the HONDIVAr (144 and 229 nm) and ArVNDIVAr (180 and 242 nm) π-systems. Bathochromic shifts can be adjusted within the broad wavelength range by introducing 4′-substituents, either electron-withdrawing group (NO2) or electron-donating group (NMe2), in the phenyl group of aryl ethylenes. ArVNDIVArs show bigger bathochromic shifts than HONDIVArs.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b02140

DOI: 10.1021/acs.joc.7b02140

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