One-pot synthesis and applications of two asymmetrical benzoxanthene dyes

Yimin Guo; Xiuping Wang; Weimin Liu; Xiuli Zheng; Haohui Ren; Jiasheng Wu; Jiechao Ge; Wenjun Zhang; Chun-Sing Lee; Pengfei Wang

doi:10.1016/j.dyepig.2022.110152

One-pot synthesis and applications of two asymmetrical benzoxanthene dyes

Yimin Guo (Co-first Author)
, Xiuping Wang (Co-first Author)
, Weimin Liu^*
, Xiuli Zheng
, Haohui Ren
, Jiasheng Wu
, Jiechao Ge
, Wenjun Zhang
, Chun-Sing Lee
, Pengfei Wang^*

^*Corresponding author for this work

Research output: Journal Publications and Reviews › RGC 21 - Publication in refereed journal › peer-review

3 Citations (Scopus)

Abstract

Two asymmetrical benzoxanthene dyes (BP-1 and BP-2) were designed and synthesized by a convenient one-step procedure from naphthaldehyde and m-aminophenol precursors. These dyes showed long-wavelength absorption, near-infrared emission (>650 nm), and large Stokes shifts (>90 nm) because of the asymmetrical introduction of the benzene ring into the xanthene structure. BP-1 exhibited high fluorescence quantum yield in organic solvents, whereas BP-2 showed very weak fluorescence due to the photoinduced electron transfer of 9-substituted groups. Cell experiments indicated that BP-1 with crescent-shape structure showed lower cytotoxicity and higher photostability than BP-2 and could rapidly stain RNA in nucleoli at low concentration.

Original language	English
Article number	110152
Journal	Dyes and Pigments
Volume	200
Online published	2 Feb 2022
DOIs	https://doi.org/10.1016/j.dyepig.2022.110152
Publication status	Published - Apr 2022

Research Keywords

Benzoxanthene dyes
Fluorescent imaging
Near-infrared emission
Photoinduced electron transfer
RNA dye

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10.1016/j.dyepig.2022.110152

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@article{c99325e0bba942e2bf22b2278ca3a85d,

title = "One-pot synthesis and applications of two asymmetrical benzoxanthene dyes",

abstract = "Two asymmetrical benzoxanthene dyes (BP-1 and BP-2) were designed and synthesized by a convenient one-step procedure from naphthaldehyde and m-aminophenol precursors. These dyes showed long-wavelength absorption, near-infrared emission (>650 nm), and large Stokes shifts (>90 nm) because of the asymmetrical introduction of the benzene ring into the xanthene structure. BP-1 exhibited high fluorescence quantum yield in organic solvents, whereas BP-2 showed very weak fluorescence due to the photoinduced electron transfer of 9-substituted groups. Cell experiments indicated that BP-1 with crescent-shape structure showed lower cytotoxicity and higher photostability than BP-2 and could rapidly stain RNA in nucleoli at low concentration.",

keywords = "Benzoxanthene dyes, Fluorescent imaging, Near-infrared emission, Photoinduced electron transfer, RNA dye",

author = "Yimin Guo and Xiuping Wang and Weimin Liu and Xiuli Zheng and Haohui Ren and Jiasheng Wu and Jiechao Ge and Wenjun Zhang and Chun-Sing Lee and Pengfei Wang",

year = "2022",

month = apr,

doi = "10.1016/j.dyepig.2022.110152",

language = "English",

volume = "200",

journal = "Dyes and Pigments",

issn = "0143-7208",

publisher = "Elsevier B.V.",

}

TY - JOUR

T1 - One-pot synthesis and applications of two asymmetrical benzoxanthene dyes

AU - Guo, Yimin

AU - Wang, Xiuping

AU - Liu, Weimin

AU - Zheng, Xiuli

AU - Ren, Haohui

AU - Wu, Jiasheng

AU - Ge, Jiechao

AU - Zhang, Wenjun

AU - Lee, Chun-Sing

AU - Wang, Pengfei

PY - 2022/4

Y1 - 2022/4

N2 - Two asymmetrical benzoxanthene dyes (BP-1 and BP-2) were designed and synthesized by a convenient one-step procedure from naphthaldehyde and m-aminophenol precursors. These dyes showed long-wavelength absorption, near-infrared emission (>650 nm), and large Stokes shifts (>90 nm) because of the asymmetrical introduction of the benzene ring into the xanthene structure. BP-1 exhibited high fluorescence quantum yield in organic solvents, whereas BP-2 showed very weak fluorescence due to the photoinduced electron transfer of 9-substituted groups. Cell experiments indicated that BP-1 with crescent-shape structure showed lower cytotoxicity and higher photostability than BP-2 and could rapidly stain RNA in nucleoli at low concentration.

AB - Two asymmetrical benzoxanthene dyes (BP-1 and BP-2) were designed and synthesized by a convenient one-step procedure from naphthaldehyde and m-aminophenol precursors. These dyes showed long-wavelength absorption, near-infrared emission (>650 nm), and large Stokes shifts (>90 nm) because of the asymmetrical introduction of the benzene ring into the xanthene structure. BP-1 exhibited high fluorescence quantum yield in organic solvents, whereas BP-2 showed very weak fluorescence due to the photoinduced electron transfer of 9-substituted groups. Cell experiments indicated that BP-1 with crescent-shape structure showed lower cytotoxicity and higher photostability than BP-2 and could rapidly stain RNA in nucleoli at low concentration.

KW - Benzoxanthene dyes

KW - Fluorescent imaging

KW - Near-infrared emission

KW - Photoinduced electron transfer

KW - RNA dye

UR - https://www.scopus.com/pages/publications/85124020095

UR - https://www.scopus.com/record/pubmetrics.uri?eid=2-s2.0-85124020095&origin=recordpage

U2 - 10.1016/j.dyepig.2022.110152

DO - 10.1016/j.dyepig.2022.110152

M3 - RGC 21 - Publication in refereed journal

SN - 0143-7208

VL - 200

JO - Dyes and Pigments

JF - Dyes and Pigments

M1 - 110152

ER -

One-pot synthesis and applications of two asymmetrical benzoxanthene dyes

Abstract

Research Keywords

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