Citation: Peng-Cheng Shi, Xin-Dong Jiang, Rui-Na Gao, Yuan-Yuan Dou, Wei-Li Zhao. Synthesis and application of Vis/NIR dialkylaminophenylbuta-1, 3-dienyl borondipyrromethene dyes[J]. Chinese Chemical Letters, ;2015, 26(7): 834-838. doi: 10.1016/j.cclet.2014.11.010 shu

Synthesis and application of Vis/NIR dialkylaminophenylbuta-1, 3-dienyl borondipyrromethene dyes

1.
a The Key Laboratory for Special Functional Materials, Ministry of Education, Henan University, Kaifeng 475004, China;
2.
b College of Applied Chemistry, Shenyang University of Chemical Technology, Shenyang 110142, China

Corresponding author: Xin-Dong Jiang, Wei-Li Zhao,
Received Date: 11 September 2014
Available Online: 20 October 2014
Fund Project: This work was supported by NNSFC (No. 21372063) (No. 21372063) the Foundation of the Education Department of Henan Province for Science and Technology Research Projects (No. 13A150046) (No. PCS IRT1126)

Mono- and bis-dialkylaminophenylbuta-1,3-dienyl boron-dipyrromethenes (BODIPYs) 1-12 were synthesized in 36%-42% yields by a Knoevenagel-type condensation. The absorption and emission maxima (λ_labs = 614-739 nm; (λ_lem = 655-776 nm in CHCl₃) of 1-12 covered from the visuble to the nearinfrared region. Probe 1 was ratiometric Vis pH probes. Such probe was almost non-fluorescent. Upon the protonation of the tertiary amine function of 1, the strong fluorescence (φ_f = 0.97) was released and the florescence intensity was dramatically increased by one thousand folds. The sharp isosbestic points were discovered at 590 nm, which was a ratiometric pH probe.
- BODIPY,
- Near-infrared,
- Fluorescent dyes,
- Spectroscopic properties
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