A series of six new 2,2'-bithiophene-functionalized diketopyrrolopyrrole (DPP) dyes 7a-f bearing different electron-donating and electron-withdrawing substituents at the terminal thiophene units was synthesized by palladium-catalyzed cross-coupling reactions. The to date unknown diiodinated DPP 2 and the corresponding boronic ester derivative 3 could be prepared in high yields, and these are shown to be versatile building blocks for the synthesis of DPP-based molecular materials by Negishi, Stile, and Suzuki coupling. The influence of the peripheral substituents on the optical and electrochemical properties of the present series of DPP dyes 7a-f were investigated by UV/vis and steady-state fluorescence spectroscopy and cyclic voltammetry, revealing an appreciable effect on the electronic nature of these dyes. The diamino-substituted DPP derivative 7e exhibits a strong absorption band reaching in the near-infrared (NIR) region, which is a highly desirable feature for application in organic photovoltaics.
机构:
Hong Kong Baptist Univ, Ctr Adv Luminescence Mat, Kowloon Tong, Hong Kong, Peoples R China
Hong Kong Baptist Univ, Dept Chem, Kowloon Tong, Hong Kong, Peoples R ChinaUniv Rennes 1, CNRS, CPM, F-35042 Rennes, France
机构:
Tech Univ Clausthal, Inst Organ Chem, D-38678 Clausthal Zellerfeld, GermanyUniv Rennes 1, CNRS, CPM, F-35042 Rennes, France
Kaufmann, Dieter
Wong, Wai-Yeung
论文数: 0引用数: 0
h-index: 0
机构:
Hong Kong Baptist Univ, Ctr Adv Luminescence Mat, Kowloon Tong, Hong Kong, Peoples R China
Hong Kong Baptist Univ, Dept Chem, Kowloon Tong, Hong Kong, Peoples R ChinaUniv Rennes 1, CNRS, CPM, F-35042 Rennes, France
机构:
Hong Kong Baptist Univ, Ctr Adv Luminescence Mat, Kowloon Tong, Hong Kong, Peoples R China
Hong Kong Baptist Univ, Dept Chem, Kowloon Tong, Hong Kong, Peoples R ChinaUniv Rennes 1, CNRS, CPM, F-35042 Rennes, France
机构:
Tech Univ Clausthal, Inst Organ Chem, D-38678 Clausthal Zellerfeld, GermanyUniv Rennes 1, CNRS, CPM, F-35042 Rennes, France
Kaufmann, Dieter
Wong, Wai-Yeung
论文数: 0引用数: 0
h-index: 0
机构:
Hong Kong Baptist Univ, Ctr Adv Luminescence Mat, Kowloon Tong, Hong Kong, Peoples R China
Hong Kong Baptist Univ, Dept Chem, Kowloon Tong, Hong Kong, Peoples R ChinaUniv Rennes 1, CNRS, CPM, F-35042 Rennes, France