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Reducing-Agent-Free Barton-Kellogg Synthesis of Bis(fluorenylidene)quinacridanes with Chromic and NIR Absorption
Xue-Lin Zheng1, Shinobu Aoyagi2, Yutaka Matsuo1,3
1Department of Chemical Systems Engineering, Graduate School of Engineering, Nagoya University, Nagoya 464-8603, Japan.
Abstract:
We report the stepwise synthesis of sterically hindered olefins comprising quinacridone and fluorene units via reducing-agent-free Barton-Kellogg olefination. The monosubstituted product (mono-FQA-S) exhibits distinct mechanochromic behavior, while the bis-substituted derivative (double-FQA) displays near-infrared absorption with a maximum wavelength at 869 nm. Their photophysical and electrochemical properties were systematically investigated. X-ray diffraction characterized the double-FQA structure. Space-charge-limited current (SCLC) measurements showed that double-FQA could be used as hole transport material. Their photophysical and electrochemical properties were systematically investigated.
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