We present a streamlined methodology that integrates regioselective tetrahalogen-BODIPY and o-hydroxyphenylboronic acid in a one-pot process, leveraging S_NAr nucleophilic substitution in conjunction with Suzuki coupling to afford diarenofuran [b]-fused BODIPYs (DBFB1–9) with commendable yields (85–95%) and short reaction times (0.5–1.0 h). X-ray structure analyses of DBFB5,7–9 elucidate that these diarenofuran[b]-fused BODIPYs adopt a “butterfly” conformation, maintaining a highly rigid planarity. A comprehensive examination of the spectroscopic and electrochemical properties of these diarenofuran[b]-fused BODIPY derivatives, incorporating various substituents, reveals intriguing characteristics, including pronounced absorption and emission in the near-infrared region (NIR), elevated fluorescence quantum yields (Φ_F = 75–89% in dichloromethane), and tunable HOMO–LUMO levels. Remarkably, compared to DBFB1–8, DBFB9 possesses a large extended π-conjugated system, resulting in significant red shifts in its absorption and emission maxima, reaching 623 and 635 nm, respectively, and a reduced HOMO–LUMO gap. Despite this substantial structural expansion, DBFB9 maintains a surprisingly high fluorescence quantum yield (Φ_F = 80%), underscoring its exceptional photophysical performance and strong potential for applications requiring efficient NIR emission and robust fluorescence retention.

中文翻译：

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Diarenofuran[b] -fused BODIPYs：一锅法 SNAr-Suzuki 合成和性质


我们提出了一种简化的方法，该方法将区域选择性四卤素-BODIPY 和邻羟基苯硼酸整合到一个一锅法中，利用 S_NAr 亲核取代与 Suzuki 偶联相结合，得到二烯基呋喃 [b] 融合的 BODIPY （DBFB1-9），产量值得称赞 （85-95%） 和反应时间短 （0.5-1.0 h）。DBFB5,7-9 的 X 射线结构分析阐明，这些淀粉呋喃 [b] 融合的 BODIPY 采用“蝶形”构象，保持高度刚性的平面性。对这些二呋喃[b]融合的 BODIPY 衍生物（包含各种取代基）的光谱和电化学性质进行全面检查，揭示了有趣的特性，包括在近红外区域 （NIR） 中显着的吸收和发射、荧光量子产率升高（Φ_F = 75-89% 在二氯甲烷中）和可调的 HOMO-LUMO 水平。值得注意的是，与 DBFB1-8 相比，DBFB9 具有较大的扩展π共轭系统，导致其最大吸收和发射波长发生显著的红移，分别达到 623 和 635 nm，并且 HOMO-LUMO 间隙减小。尽管结构进行了大幅扩展，但 DBFB9 仍保持了令人惊讶的高荧光量子产率 （Φ_F = 80%），这凸显了其卓越的光物理性能以及在需要高效 NIR 发射和强大荧光保留能力的应用中的巨大潜力。