研究目的
To prepare twisted 'X' shaped polycyclic aromatic hydrocarbons (PAHs) through annulation of hexacene with benzoanthracene on the zigzag edge, and investigate their photophysical properties and self-assembly properties, aiming to tune self-assembly ability or introduce functional groups without altering photophysical properties.
研究成果
The twisted 'X' shaped PAHs exhibit stable photophysical properties that are minimally affected by peripheral functionalization, while their self-assembly behavior can be tuned from dimerization to one-dimensional π-stacking. This provides insights for designing stable PAHs with tailored assembly properties without compromising electronic structures, with potential applications in organic electronics and materials science.
研究不足
The study is limited to specific 'X' shaped PAH derivatives; generalizability to other PAH structures may require further investigation. The electron mobility measured for 1e was relatively low (3.1×10^-4 cm2 V?1 s?1), attributed to weak crystalline nature of spin-coated films, indicating potential optimization in film processing for better device performance.
1：Experimental Design and Method Selection:
The study involved the synthesis of 'X' shaped PAHs using various coupling reactions (e.g., Suzuki cross-coupling, Sonogashira coupling, Glaser self-coupling, cyclization, and cyclodehydrogenation), followed by characterization of their optical, electrochemical, and self-assembly properties. Theoretical calculations (e.g., CASSCF, DFT) were employed to understand electronic structures and aromaticity.
2：Sample Selection and Data Sources:
Compounds were synthesized step-by-step starting from precursors like 3,5-di-tert-butylbromobenzene and pyrene derivatives. Single crystals for X-ray diffraction were grown by slow diffusion of acetone vapor into CHCl3 solutions.
3：List of Experimental Equipment and Materials:
Instruments included NMR spectrometers (e.g., 400 MHz, 500 MHz), UV/Vis spectrophotometers, fluorescence spectrometers, cyclic voltammetry setups, ESR spectrometers, SEM, TEM, PXRD, and MALDI-TOF mass spectrometers. Chemicals included various boronic acids, catalysts (e.g., Pd(PPh3)4, PtCl2), and solvents.
4：Experimental Procedures and Operational Workflow:
Synthesis involved multiple steps with specific conditions (e.g., temperatures, catalysts, solvents) as detailed in Scheme 1. Optical properties were measured in solutions like CH2Cl2, electrochemical studies used CH2Cl2 with TBAPF6 as electrolyte, and self-assembly studies involved concentration and temperature-dependent measurements.
5：Optical properties were measured in solutions like CH2Cl2, electrochemical studies used CH2Cl2 with TBAPF6 as electrolyte, and self-assembly studies involved concentration and temperature-dependent measurements.
Data Analysis Methods:
5. Data Analysis Methods: Data were analyzed using software for NMR, UV/Vis, fluorescence lifetime measurements, cyclic voltammetry, and theoretical calculations (e.g., B3LYP/6-31G(d,p) for DFT). Binding constants were calculated from concentration-dependent UV/Vis data.
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