Synthesis of mono-(p-dimethylamino)styryl-containing BOPHY dye for a turn-on pH sensor

作者: Xin-Dong Jiang , Yajun Su , Shuai Yue , Chen Li , Haifeng Yu

DOI: 10.1039/C4RA15914D

关键词:

摘要: Mono-substitutional bis(difluoroboron)1,2-bis((1H-pyrrol-2-yl)methylene)hydrazine (BOPHY) 3a with a (p-dimethylamino)styryl group in the α-position was confirmed to be synthesized by Knoevenagel-type condensation. Dimethylamino-containing BOPHY dye is almost non-fluorescent ICT effect. Upon protonation of tertiary amine function 3a, strong fluorescence (Φf = 0.98) released and intensity dramatically increased one thousand fold. can used as pH probe.

参考文章(60)
Kenneth C. Wong, Review of NMR Spectroscopy: Basic Principles, Concepts and Applications in Chemistry Journal of Chemical Education. ,vol. 91, pp. 1103- 1104 ,(2014) , 10.1021/ED500324W
Ting Jiang, Ping Zhang, Changjiang Yu, Jian Yin, Lijuan Jiao, En Dai, Jun Wang, Yun Wei, Xiaolong Mu, Erhong Hao, Straightforward Synthesis of Oligopyrroles through a Regioselective SNAr Reaction of Pyrroles and Halogenated Boron Dipyrrins Organic Letters. ,vol. 16, pp. 1952- 1955 ,(2014) , 10.1021/OL500507F
Abhineeshbabu Thottiparambil, P. R. Anil Kumar, Lakshmi Chakkumkumarath, Styrylcyanine-based ratiometric and tunable fluorescent pH sensors RSC Advances. ,vol. 4, pp. 56063- 56067 ,(2014) , 10.1039/C4RA10959G
Robert M Strongin, Lovemore Hakuna, Hanjing Peng, Weixuan Chen, Yunfeng Cheng, Binghe Wang, None, Thiol Reactive Probes and Chemosensors Sensors. ,vol. 12, pp. 15907- 15946 ,(2012) , 10.3390/S121115907
Lin Yuan, Weiying Lin, Kaibo Zheng, Longwei He, Weimin Huang, Far-red to near infrared analyte-responsive fluorescent probes based on organic fluorophore platforms for fluorescence imaging Chemical Society Reviews. ,vol. 42, pp. 622- 661 ,(2013) , 10.1039/C2CS35313J
Lijuan Jiao, Yayang Wu, Yin Ding, Sufan Wang, Ping Zhang, Changjiang Yu, Yun Wei, Xiaolong Mu, Erhong Hao, Conformationally restricted aza-dipyrromethene boron difluorides (aza-BODIPYs) with high fluorescent quantum yields. Chemistry-an Asian Journal. ,vol. 9, pp. 805- 810 ,(2014) , 10.1002/ASIA.201301362
Hua Lu, John Mack, Yongchao Yang, Zhen Shen, Structural modification strategies for the rational design of red/NIR region BODIPYs Chemical Society Reviews. ,vol. 43, pp. 4778- 4823 ,(2014) , 10.1039/C4CS00030G
Xingming Gao, Yanling Zhang, Binghe Wang, New Boronic Acid Fluorescent Reporter Compounds. 2. A Naphthalene-Based On−Off Sensor Functional at Physiological pH† Organic Letters. ,vol. 5, pp. 4615- 4618 ,(2003) , 10.1021/OL035783I
Wolter F. Jager, Tessel S. Hammink, Otto van den Berg, Ferdinand C. Grozema, Highly sensitive water-soluble fluorescent ph sensors based on the 7-amino-1-methylquinolinium chromophore. Journal of Organic Chemistry. ,vol. 75, pp. 2169- 2178 ,(2010) , 10.1021/JO902225K
Ralph Weissleder, Mikael J. Pittet, Imaging in the era of molecular oncology Nature. ,vol. 452, pp. 580- 589 ,(2008) , 10.1038/NATURE06917