Abstract

The reaction of dibenzo[b,e][1,4]dioxine-2,3-dicarbonitrile with sodium butoxide in butyl alcohol, followed by treatment with nitric acid, gave 1H-benzo[5,6][1,4]dioxino[2,3-f]isoindole-1,3(2H)-dione, which was brought into the condensation with quinaldine to obtain (E,Z)-3-(quinolin-2-ylmethylidene)-2,3-dihydro-1H-benzo[5,6][1,4]dioxino[2,3-f]isoindol-1-one. Treatment of the latter with BF₃·Et₂O in the presence of tri­ethyl­amine in toluene afforded a new unsymmetrical BODIPY analogue, (Z)-2-(difluoroboryl)-3-(quinolin-2-ylmethylidene)-2,3-dihydro-1H-benzo[5,6][1,4]dioxino[2,3-f]isoindol-1-one. The product showed luminescence in solution with a Stokes shift of 36 nm and a high relative fluorescence quantum yield (φ = 0.72). The obtained experimental data were supported by DFT and TD-DFT calculations.

中文翻译：

---

(Z)-2-(二氟硼基)-3-(喹啉-2-基亚甲基)-2,3-二氢-1H-苯并[5,6][1,4]二恶基[2,3-]的合成及发光性能f]isoindol-1-one，一种新的不对称 BODIPY 类似物

 抽象的

二苯并[b,e][1,4]二恶英-2,3-二甲腈与丁醇钠在丁醇中反应，然后用硝酸处理，得到1H-苯并[5,6][1,4]二恶英[2,3-f]异吲哚-1,3(2H)-二酮，与喹哪啶缩合，得到(E,Z)-3-(喹啉-2-基亚甲基)-2,3-二氢- 1H-苯并[5,6][1,4]二恶英[2,3-f]异吲哚-1-酮。在三乙胺存在下，用 BF ₃ ·Et ₂ O 处理后者，得到一种新的不对称 BODIPY 类似物，(Z)-2-(二氟硼基)-3-(喹啉-2-基亚甲基)-2,3-二氢-1H-苯并[5,6][1,4]二恶英[2,3-f]异吲哚-1-酮。该产品在溶液中发光，斯托克斯位移为 36 nm，相对荧光量子产率较高（φ = 0.72）。获得的实验数据得到了DFT和TD-DFT计算的支持。