Synthesis and spectral properties of new boron dipyrromethene dyes

Binchen Guo; Xiaojun Peng; Aijun Cui; Yunkou Wu; Maozhong Tian; Lizhu Zhang; Xiaoqiang Chen; Yunling Gao

doi:10.1016/j.dyepig.2005.11.007

Synthesis and spectral properties of new boron dipyrromethene dyes

Binchen Guo, Xiaojun Peng, Aijun Cui, Yunkou Wu, Maozhong Tian, Lizhu Zhang, Xiaoqiang Chen, Yunling Gao

Advanced Imaging Research Center

Research output: Contribution to journal › Article › peer-review

38 Scopus citations

Abstract

New BODIPY dyes have been synthesized via the condensation of R-CH₂COCl (R = H, Br, Cl and Et₂N) with 2,4-dimethylpyrrole and the coordination with BF₃ etherate. The acetyl chlorides with electron-withdrawing substituents (R = Br or Cl) are easier to react with the 2,4-dimethylpyrrole to form the related dyes and make a red-shift in absorbance and fluorescence maximum. Dye 4 (R = Et₂N), based on PET mechanism, exhibits good properties as a pH fluorescent sensor with a pK_a of 8.74 and a 15-fold fluorescence enhancement in the pH range of 9.38-7.60.

Original language	English (US)
Pages (from-to)	206-210
Number of pages	5
Journal	Dyes and Pigments
Volume	73
Issue number	2
DOIs	https://doi.org/10.1016/j.dyepig.2005.11.007
State	Published - 2007

Keywords

BODIPY
Biological label
Fluorescent dyes
PET
pH probe

ASJC Scopus subject areas

Chemical Engineering(all)
Process Chemistry and Technology

Access to Document

10.1016/j.dyepig.2005.11.007

Cite this

@article{540a609ebe664aa584db92c87638c9d0,

title = "Synthesis and spectral properties of new boron dipyrromethene dyes",

abstract = "New BODIPY dyes have been synthesized via the condensation of R-CH2COCl (R = H, Br, Cl and Et2N) with 2,4-dimethylpyrrole and the coordination with BF3 etherate. The acetyl chlorides with electron-withdrawing substituents (R = Br or Cl) are easier to react with the 2,4-dimethylpyrrole to form the related dyes and make a red-shift in absorbance and fluorescence maximum. Dye 4 (R = Et2N), based on PET mechanism, exhibits good properties as a pH fluorescent sensor with a pKa of 8.74 and a 15-fold fluorescence enhancement in the pH range of 9.38-7.60.",

keywords = "BODIPY, Biological label, Fluorescent dyes, PET, pH probe",

author = "Binchen Guo and Xiaojun Peng and Aijun Cui and Yunkou Wu and Maozhong Tian and Lizhu Zhang and Xiaoqiang Chen and Yunling Gao",

note = "Funding Information: This work was supported by the Education Ministry of China and National Science Foundation of China (project 20128005, 20376010 and 20472012). ",

year = "2007",

doi = "10.1016/j.dyepig.2005.11.007",

language = "English (US)",

volume = "73",

pages = "206--210",

journal = "Dyes and Pigments",

issn = "0143-7208",

publisher = "Elsevier BV",

number = "2",

}

TY - JOUR

T1 - Synthesis and spectral properties of new boron dipyrromethene dyes

AU - Guo, Binchen

AU - Peng, Xiaojun

AU - Cui, Aijun

AU - Wu, Yunkou

AU - Tian, Maozhong

AU - Zhang, Lizhu

AU - Chen, Xiaoqiang

AU - Gao, Yunling

N1 - Funding Information: This work was supported by the Education Ministry of China and National Science Foundation of China (project 20128005, 20376010 and 20472012).

PY - 2007

Y1 - 2007

N2 - New BODIPY dyes have been synthesized via the condensation of R-CH2COCl (R = H, Br, Cl and Et2N) with 2,4-dimethylpyrrole and the coordination with BF3 etherate. The acetyl chlorides with electron-withdrawing substituents (R = Br or Cl) are easier to react with the 2,4-dimethylpyrrole to form the related dyes and make a red-shift in absorbance and fluorescence maximum. Dye 4 (R = Et2N), based on PET mechanism, exhibits good properties as a pH fluorescent sensor with a pKa of 8.74 and a 15-fold fluorescence enhancement in the pH range of 9.38-7.60.

AB - New BODIPY dyes have been synthesized via the condensation of R-CH2COCl (R = H, Br, Cl and Et2N) with 2,4-dimethylpyrrole and the coordination with BF3 etherate. The acetyl chlorides with electron-withdrawing substituents (R = Br or Cl) are easier to react with the 2,4-dimethylpyrrole to form the related dyes and make a red-shift in absorbance and fluorescence maximum. Dye 4 (R = Et2N), based on PET mechanism, exhibits good properties as a pH fluorescent sensor with a pKa of 8.74 and a 15-fold fluorescence enhancement in the pH range of 9.38-7.60.

KW - BODIPY

KW - Biological label

KW - Fluorescent dyes

KW - PET

KW - pH probe

UR - http://www.scopus.com/inward/record.url?scp=33748421427&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=33748421427&partnerID=8YFLogxK

U2 - 10.1016/j.dyepig.2005.11.007

DO - 10.1016/j.dyepig.2005.11.007

M3 - Article

AN - SCOPUS:33748421427

SN - 0143-7208

VL - 73

SP - 206

EP - 210

JO - Dyes and Pigments

JF - Dyes and Pigments

IS - 2

ER -

Synthesis and spectral properties of new boron dipyrromethene dyes

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this