Synthesis and photophysical insights of new fused N-heterocyclic derivatives with isoquinoline skeleton

被引：8

作者：

Gherasim, Carmen ^{[1
]}

Airinei, Anton ^{[1
]}

Tigoianu, Radu ^{[1
]}

Craciun, Anda M. ^{[1
]}

Danac, Ramona ^{[2
]}

Nicolescu, Alina ^{[1
]}

Isac, Dragos Lucian ^{[1
]}

Mangalagiu, Ionel I. ^{[2
]}

机构：

[1] Petru Poni Inst Macromol Chem, Grigore Ghica Voda Alley 41A, Iasi 700487, Romania

[2] Alexandru Ioan Cuza Univ, Chem Dept, 11 Carol I Bd, Iasi 700506, Romania

来源：

JOURNAL OF MOLECULAR LIQUIDS | 2020年 / 310卷

关键词：

Pyrrolo[2,1-a]isoquinoline; Imidazo[2,1-a]isoquinoline; Fluorescence; Quantum yields; Lifetimes; TIME-RESOLVED FLUORESCENCE; STEADY-STATE;

D O I：

10.1016/j.molliq.2020.113196

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

Six new fused isoquinoline based compounds (compounds 5a-c with pyrrolo[2,1-a] isoquinoline structure and compounds 6a-c with imidazo[2,1-a]isoquinoline skeleton) have been synthesized using the [3 + 2] cycloaddition of the several in situ generated cycloimmonium ylides to ethyl propiolate or ethyl cyanoformate. All the synthesized compounds have been investigated in solution by UV-VIS absorption, steady and time-resolved fluorescence methods. The effect of the substituents on the spectral characteristics has been demonstrated. These derivatives displayed an intense emission between 360 and 420 nm. The emission quantum yields (Phi = 0.54-0.64) of pyrroloisoquinoline derivatives in dimethylsulfoxide (DMSO) were significantly higher than those of imidazoquinolines (0.03-0.16). The fluorescence decay of isoquinoline derivatives follows a biexponential law. A noticeable response of these isoquinoline derivatives to sodium hydroxide was observed. (C) 2020 Elsevier B.V. All rights reserved.

引用

页数：9

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