研究目的
Exploring the syntheses, structure, photophysical properties, and photostability of benzodipyrenes (BDPs) through an InCl3-AgNTf2 catalyzed, four-fold alkyne benzannulation reaction.
研究成果
The synthesis of benzodipyrene (BDP) derivatives through InCl3-AgNTf2-catalyzed four-fold alkyne benzannulation reactions was presented. The BDP scaffold consists of a less common and difficult to synthesize benzo[a]pyrene substructure. Both BDP molecules exhibited a blue-shift in absorbance by ca. 40 nm relative to pentacene. The described combination of cata- and peri-benzannulation strategy is an effective way to access larger acene-based PAHs with enhanced solubility and stability.
研究不足
The photochemical decomposition of BDPs in the presence of O2 and light irradiation limits their utility.
1：Experimental Design and Method Selection:
The synthesis of BDPs was achieved through an InCl3-AgNTf2 catalyzed, four-fold alkyne benzannulation reaction.
2：Sample Selection and Data Sources:
The key precursors 3a?b were isolated in modest yields through a double Suzuki reaction.
3：List of Experimental Equipment and Materials:
InCl3, AgNTf2, toluene, CDCl3, methanol.
4：Experimental Procedures and Operational Workflow:
The BDP products were isolated after treating compound 3 with the InCl3-AgNTf2 catalyst system in toluene at 100 °C for 24 hours.
5：Data Analysis Methods:
The structures of BDP 4a and its corresponding endoperoxide product were confirmed by X-ray crystallography. The optical properties were studied by absorption and emission spectroscopy.
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