Synthesis, Optical and Electrochemical Properties of Benzofuro[2,3-c]carbazoloquinol Fluorescent Dyes

Benzofuro[2,3-c]carbazoloquinol derivatives, a new type of fluorescent dyes, were derived from the corresponding quinone, and their optical and electrochemical properties were investigated by photoabsorption and fluorescence spectroscopy, cyclic voltammetry (CV) and density functional theory (DFT) c...

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Autores principales:	Yousuke OOYAMA, Kazuki OHIRA, Yusuke KAGAWA, Keiichi IMATO
Formato:	article
Lenguaje:	EN JA
Publicado:	The Electrochemical Society of Japan 2021
Materias:	benzofuro[2,3-c]carbazoloquinol photoabsorption fluorescence redox Technology T Physical and theoretical chemistry QD450-801
Acceso en línea:	https://doaj.org/article/b14a2042cb03438fa714c9bf67fff556
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spelling	oai:doaj.org-article:b14a2042cb03438fa714c9bf67fff5562021-11-05T00:17:27ZSynthesis, Optical and Electrochemical Properties of Benzofuro[2,3-c]carbazoloquinol Fluorescent Dyes2186-245110.5796/electrochemistry.21-00082https://doaj.org/article/b14a2042cb03438fa714c9bf67fff5562021-11-01T00:00:00Zhttps://www.jstage.jst.go.jp/article/electrochemistry/89/6/89_21-00082/_html/-char/enhttps://doaj.org/toc/2186-2451Benzofuro[2,3-c]carbazoloquinol derivatives, a new type of fluorescent dyes, were derived from the corresponding quinone, and their optical and electrochemical properties were investigated by photoabsorption and fluorescence spectroscopy, cyclic voltammetry (CV) and density functional theory (DFT) calculation. The quinol derivatives in 1,4-dioxane showed the photoabsorption band at around 435 nm (molar extinction coefficient (εmax) = ca. 6000–8000 M−1 cm−1) and the fluorescence band at around 520 nm (fluorescence quantum yield (Φfl) = 0.24–0.28). The CV demonstrated that the quinol derivatives exhibit an irreversible oxidation wave at around −0.28 V versus Fc/Fc+. The highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO) energy levels of the quinol derivatives which were calculated using DFT at the B3LYP/6-31G(d,p) level are in good agreement with the experimental results.Yousuke OOYAMAKazuki OHIRAYusuke KAGAWAKeiichi IMATOThe Electrochemical Society of Japanarticlebenzofuro[2,3-c]carbazoloquinolphotoabsorptionfluorescenceredoxTechnologyTPhysical and theoretical chemistryQD450-801ENJAElectrochemistry, Vol 89, Iss 6, Pp 562-566 (2021)
institution	DOAJ
collection	DOAJ
language	EN JA
topic	benzofuro[2,3-c]carbazoloquinol photoabsorption fluorescence redox Technology T Physical and theoretical chemistry QD450-801
spellingShingle	benzofuro[2,3-c]carbazoloquinol photoabsorption fluorescence redox Technology T Physical and theoretical chemistry QD450-801 Yousuke OOYAMA Kazuki OHIRA Yusuke KAGAWA Keiichi IMATO Synthesis, Optical and Electrochemical Properties of Benzofuro[2,3-c]carbazoloquinol Fluorescent Dyes
description	Benzofuro[2,3-c]carbazoloquinol derivatives, a new type of fluorescent dyes, were derived from the corresponding quinone, and their optical and electrochemical properties were investigated by photoabsorption and fluorescence spectroscopy, cyclic voltammetry (CV) and density functional theory (DFT) calculation. The quinol derivatives in 1,4-dioxane showed the photoabsorption band at around 435 nm (molar extinction coefficient (εmax) = ca. 6000–8000 M−1 cm−1) and the fluorescence band at around 520 nm (fluorescence quantum yield (Φfl) = 0.24–0.28). The CV demonstrated that the quinol derivatives exhibit an irreversible oxidation wave at around −0.28 V versus Fc/Fc+. The highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO) energy levels of the quinol derivatives which were calculated using DFT at the B3LYP/6-31G(d,p) level are in good agreement with the experimental results.
format	article
author	Yousuke OOYAMA Kazuki OHIRA Yusuke KAGAWA Keiichi IMATO
author_facet	Yousuke OOYAMA Kazuki OHIRA Yusuke KAGAWA Keiichi IMATO
author_sort	Yousuke OOYAMA
title	Synthesis, Optical and Electrochemical Properties of Benzofuro[2,3-c]carbazoloquinol Fluorescent Dyes
title_short	Synthesis, Optical and Electrochemical Properties of Benzofuro[2,3-c]carbazoloquinol Fluorescent Dyes
title_full	Synthesis, Optical and Electrochemical Properties of Benzofuro[2,3-c]carbazoloquinol Fluorescent Dyes
title_fullStr	Synthesis, Optical and Electrochemical Properties of Benzofuro[2,3-c]carbazoloquinol Fluorescent Dyes
title_full_unstemmed	Synthesis, Optical and Electrochemical Properties of Benzofuro[2,3-c]carbazoloquinol Fluorescent Dyes
title_sort	synthesis, optical and electrochemical properties of benzofuro[2,3-c]carbazoloquinol fluorescent dyes
publisher	The Electrochemical Society of Japan
publishDate	2021
url	https://doaj.org/article/b14a2042cb03438fa714c9bf67fff556
work_keys_str_mv	AT yousukeooyama synthesisopticalandelectrochemicalpropertiesofbenzofuro23ccarbazoloquinolfluorescentdyes AT kazukiohira synthesisopticalandelectrochemicalpropertiesofbenzofuro23ccarbazoloquinolfluorescentdyes AT yusukekagawa synthesisopticalandelectrochemicalpropertiesofbenzofuro23ccarbazoloquinolfluorescentdyes AT keiichiimato synthesisopticalandelectrochemicalpropertiesofbenzofuro23ccarbazoloquinolfluorescentdyes
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Synthesis, Optical and Electrochemical Properties of Benzofuro[2,3-c]carbazoloquinol Fluorescent Dyes

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