Electron rich substituted 8-carboline derivatives: Synthesis and photophysical properties

被引:2
作者
Maret, Corentin [1 ]
Chebourou, Sarah [1 ]
De Nicola, Antoinette [1 ]
Papineau, Thomas V. [2 ]
Vacher, Morgane [2 ]
Jacquemin, Denis [2 ,3 ]
Ulrich, Gilles [1 ]
机构
[1] Ecole Chim Polymeres Materiaux Strasbourg ECPM, Inst Chim & Procedes Energie Environm & Sante ICPE, Grp Chim Organ Mat Biol & Opt COMBO, CNRS UMR 7515, 25 Rue Becquerel, F-67087 Strasbourg 02, France
[2] Nantes Univ, CNRS, CEISAM, UMR 6230, F-44000 Nantes, France
[3] Inst Univ France IUF, F-75005 Paris, France
关键词
8-carboline; Photoluminescence; TD-DFT calculations; BETA-CARBOLINE ALKALOIDS; FLUORESCENCE; WATER;
D O I
10.1016/j.dyepig.2023.111640
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
We report the synthesis and characterisation of known and novel analogues of 8-carboline, a naturally occurring alkaloid. Striving to induce changes in the optical properties of carboline, we first focus on substitutions at position 1 before exploring other positions. The 8-carbolines were synthesized using, on the one hand, post-synthetic functionalization of biosourced products and, on the other hand, total synthesis of the desired com-pounds. Our strategy mainly relies on the well-known Pictet-Spengler reaction, followed by aromatization using different techniques. Post functionalization were performed by Knoevenagel condensation or pallado-catalyzed cross-coupling. The measured UV-visible and fluorescence spectra show unexpected results with large shifts obtained when changing a few substituents only. For instance, the replacement of the aryl by a styryl substituent induces a bathochromic shift as large as 70 nm. This allowed controlling the position of the emission on a broad range (from 370 to 650 nm). Additionally, protonation of the compounds leads to profound changes in the spectroscopic properties. We indeed observe for some compounds a bathochromic shift in the emission as large as 200 nm upon protonation. The main experimental results are rationalized using theoretical calculations.
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页数:8
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