Tigreros Alexis, Bedoya-Malagón Camilo, Valencia Alejandra, Núñez-Portela Mayerlin, Portilla Jaime
Bioorganic Compounds Research Group, Department of Chemistry, Universidad de Los Andes Carrera 1 No. 18A-10 Bogotá 111711 Colombia
Quantum Optics Laboratory, Department of Physics, Universidad de Los Andes Carrera 1 No. 18A-10 Bogotá Colombia.
RSC Adv. 2023 Jan 9;13(3):1757-1764. doi: 10.1039/d2ra07498b. eCollection 2023 Jan 6.
Herein, we report the synthesis and photophysical characterization of the novel tris(4-(2,2-difluoro-6-methyl-2-1λ,3,2λ-dioxaborinin-4-yl)phenyl)amine trimeric probe (A2) the reaction between triphenylamine (1), acetic anhydride, and BF·OEt implying the twelve new bond formation in a one-pot manner. This highly fluorescent compound in solution ( up to 0.91 at 572 nm) and solid state ( = 0.24 at 571 nm) showed a better solvatofluorochromism than its analog monomeric A1 due to symmetry-broken charge transfer, which is consistent with high solvent dipolarity (SdP) response in Catalán's multiparametric regression. Notably, A2 had a high sensibility and selectivity for CN or F in solution (LODCN/F = 0.18/0.70 μM), and CN can be discriminated from F by the reaction of A2 with 3.0 equiv. of CN. In addition, A2 was impregnated on filter paper to prepare test strips that were applied to naked-eye qualitative sensing of CN or F. Finally, the octupolar system in A2 allows for better action of two-photon excitation cross-section values when compared with that of the dipolar structure in A1. These findings provide further information for the design of new efficient two-photon absorption dyes.
在此，我们报道了新型三聚体探针三（4-（2,2-二氟-6-甲基-2-1λ,3,2λ-二氧硼杂环戊硼烷-4-基）苯基）胺（A2）的合成及其光物理性质表征，其由三苯胺（1）、乙酸酐和BF·OEt反应一锅法形成12个新键。这种在溶液中（572nm处荧光量子产率高达0.91）和固态下（571nm处荧光量子产率为0.24）具有高荧光性的化合物，由于对称性破缺的电荷转移，比其类似的单体A1表现出更好的溶剂化显色性，这与Catalán多参数回归中的高溶剂偶极矩（SdP）响应一致。值得注意的是，A2在溶液中对CN或F具有高灵敏度和选择性（CN/F的检测限为0.18/0.70μM），并且通过A2与3.0当量的CN反应可将CN与F区分开来。此外，将A2浸渍在滤纸上制备测试条，用于对CN或F进行肉眼定性传感。最后，与A1中的偶极结构相比，A2中的八极体系在双光子激发截面值方面表现出更好的性能。这些发现为新型高效双光子吸收染料的设计提供了更多信息。
