Using pyrrolizine-fused bipolar PAHs as a new strategy towards efficient red and NIR emissive dyes
Using pyrrolizine-fused bipolar PAHs as a new strategy towards efficient red and NIR emissive dyes
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DOI：
10.1039/d3qo01914d
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发表时间：
2023-12-04
影响因子：
5.4
通讯作者：
Lindner，Marcin
中科院分区：
文献类型：
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作者：
Bartkowski，Krzysztof;Gupta，Abhishek Kumar;Lindner，Marcin
我们报道了第一个吡咯里嗪包埋多环芳烃体系的合成和表征。通过一锅级联的Suzuki/Boc脱保护/Buchwald-Hartwig变换，成功地合成了基于萘酰亚胺和吲哚熔融的双极核。以芳香胺为给体亚基对杂环上未占据的β位进行简单的后官能化处理，得到了一系列基于给体-受体结构的染料。有效地缩小了HOMO-LUMO能隙，并通过改变施主强度来调节它，以及稳定了π-NMI核心内的∼共轭，为近红外发射提供了一条途径，不仅在溶液中(∼740 nm)，而且在固体中(PM700 Nm)。
We report the synthesis and characterization of the first pyrrolizine-embedded PAH systems. The bipolar core, based on a naphthalimide and indole fusion, was successfully synthesized through a one-pot cascade of Suzuki/Boc deprotection/Buchwald–Hartwig transformations. A facile post-functionalization of the unoccupied β-position of the heterocycle with aromatic amines as donor subunits led to a set of donor–acceptor architecture-based dyes. Effective narrowing of the HOMO–LUMO gap, along with its tuning by changing donor strength together with stabilization of π conjugation within the pyrrolizine–NMI core, provided a route to near-infrared (NIR) emission not only in solution (∼740 nm) but also in the solid-state (∼700 nm).