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Synthesis and Optical and Electrochemical Properties of Julolidine-Structured pyrido[3,4-b]indole Dye

Synthesis and Optical and Electrochemical Properties of Julolidine-Structured pyrido[3,4-b]indole Dye

Toshiaki Enoki, Keishi Matsuo, Joji Ohshita, Yousuke Ooyama

Phys Chem Chem Phys. 2017 Feb 1;19(5):3565-3574.

PMID: 28093592

Abstract:

The julolidine-structured pyrido[3,4-b]indole dye ET-1 has been newly designed and developed as a small D-A fluorescent dye. ET-1 showed bathochromic shifts of the fluorescence band upon changing from aprotic solvents to protic solvents, as well as positive fluorescence solvatochromism. Moreover, it was found that ET-1 can form a 1 : 1 Py(N)-B complex with boron trifluoride and a hydrogen-bonded proton transfer (Py(N)-H) complex with trifluoroacetic acid, which exhibit photoabsorption and fluorescence bands at a longer wavelength region than the pristine ET-1. Based on optical (photoabsorption and fluorescence spectroscopy) and electrochemical (cyclic voltammetry) measurements, Lippert-Mataga plots, 1H NMR spectral measurement and density functional theory (DFT) calculation, this work indicated that the Py(N)-B complex or the Py(N)-H complex is effectively formed and stable in solution. This is due to the strong Py(N)-B interaction or Py(N)-hydrogen-bond, which can be attributed to the enhanced basicity or the accumulated electron density on the nitrogen atom of the pyridine ring caused by the introduction of a julolidine (quinolizidine) moiety as a strong electron-donating group. We propose that the D-A-type dye ET-1 based on the julolidine-structured pyrido[3,4-b]indole possesses the ability to act as a calorimetric and fluorescent sensor for Brønsted and Lewis acids.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP479594	Julolidine		479-59-4	Price

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