Spiro-Fused Perylene Diimide Arrays

Gao G, Liang N, Geng H, Jiang W, Fu H, Feng J, Hou J, Feng X, Wang Z (2017)

Publication Type: Journal article

Publication year: 2017

Journal

Journal of the American Chemical Society American Chemical Society

Book Volume: 139

Pages Range: 15914-15920

Journal Issue: 44

DOI: 10.1021/jacs.7b09140

Abstract

The straightforward palladium-catalyzed synthesis protocol toward spiro-fused perylene diimides is developed. The reaction involves two palladium-catalyzed C-H activations and 4-fold C-C bond formation sequence from readily available precursors. This facile and step-economic approach also provides another convenient access to ethylene-bridged dimer (NDP) and further π-extended spiro system (SNTP). In addition, the molecular structure of spirodiperylenetetraimide (SDP) is illustrated to show a three-dimensional (3D) cruciform configuration, and its absorbance is distinctly red-shifted due to the significant spiroconjugation effect. With combined properties of broadened and intensive absorption, aligned LUMO levels, and unique molecular geometry, the spiro-fused PDI system represents a new kind of high-performance semiconducting framework as the electron acceptor in high-efficiency organic solar cells.

Involved external institutions

Chinese Academy of Sciences (CAS) / 中国科学院 CN China (CN) Technische Universität Dresden DE Germany (DE)

How to cite

APA:

Gao, G., Liang, N., Geng, H., Jiang, W., Fu, H., Feng, J.,... Wang, Z. (2017). Spiro-Fused Perylene Diimide Arrays. Journal of the American Chemical Society, 139(44), 15914-15920. https://doi.org/10.1021/jacs.7b09140

MLA:

Gao, Guangpeng, et al. "Spiro-Fused Perylene Diimide Arrays." Journal of the American Chemical Society 139.44 (2017): 15914-15920.

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