基于吲哚的氮杂[n]薁（n=5,6）具有蓝紫色荧光和双光子吸收（TPA）。

Indole-Based Aza[n]helicenes (n=5, 6) with Violet-Blue Fluorescence and Two-Photon Absorption (TPA).

机构信息

State Key Laboratory of Crystal Materials, Shandong University, Jinan, 250100, P. R. China.

出版信息

Chempluschem. 2020 Apr;85(4):742-750. doi: 10.1002/cplu.202000178.

DOI:10.1002/cplu.202000178

Abstract

A series of indole-based helicenes, namely, 15-hexyl-15H-tetraphenyl[1,2-e]indole (HTPI), 14-hexyl-14H-benzo[4',5']thieno [2',3':7,8]naphtha[1,2-e]indole (HBTNI), 7-hexyl-7H-indolo[5,4-k] phenanthridine (HIPD) and 3-hexyl-3H-phenanthro[4,3-e]indole (HPI) were successfully synthesized by three- or four-step reactions. They exhibited good solubility and high thermal stability of T =247, 388, 294 and 251 °C, respectively. These compounds emit violet-blue light with maximum emission peaks at 415, 397, 397 and 391 nm in hexane. Among them, HBTNI had excellent thermal stability, narrow and sharp emission peaks, and highest photoluminescence quantum yield (0.32). Thus, HBTNI was an ideal candidate for the violet-blue emitters of OLEDs. Furthermore, the four compounds had two-photon absorption and two-photon excited fluorescence. HTPI showed the maximum TPA with the TPA cross-section (δ) of 171.5 GM at 770 nm. They were rare examples of helicenes with both violet-blue emission and TPA.

摘要

一系列吲哚类螺旋芳烃，即 15-己基-15H-四苯基[1,2-e]吲哚（HTPI）、14-己基-14H-苯并[4',5']噻吩[2',3':7,8]萘[1,2-e]吲哚（HBTNI）、7-己基-7H-吲哚并[5,4-k]菲啶（HIPD）和 3-己基-3H-菲并[4,3-e]吲哚（HPI），通过三或四步反应成功合成。它们具有良好的溶解性和较高的热稳定性，T 值分别为 247、388、294 和 251°C。这些化合物在己烷中发射出蓝紫光，最大发射峰分别位于 415、397、397 和 391nm。其中，HBTNI 具有出色的热稳定性、窄而尖锐的发射峰和最高的光致发光量子产率（0.32）。因此，HBTNI 是 OLED 中理想的蓝紫光发射体候选材料。此外，这四种化合物还具有双光子吸收和双光子激发荧光。HTPI 在 770nm 处表现出最大的双光子吸收截面（δ），为 171.5 GM。它们是具有蓝紫光发射和双光子吸收的螺旋芳烃的罕见实例。