TY - JOUR
T1 - Ultrasensitive reversible chromophore reaction of BODIPY functions as high ratio double turn on probe
AU - Hu, Dehui
AU - Zhang, Tao
AU - Li, Shayu
AU - Yu, Tianjun
AU - Zhang, Xiaohui
AU - Hu, Rui
AU - Feng, Jiao
AU - Wang, Shuangqing
AU - Liang, Tongling
AU - Chen, Jianming
AU - Sobenina, Lyubov N.
AU - Trofimov, Boris A.
AU - Li, Yi
AU - Ma, Jinshi
AU - Yang, Guoqiang
N1 - Publisher Copyright:
© 2018 The Author(s).
PY - 2018/12/1
Y1 - 2018/12/1
N2 - Chromophore reactions with changes to conjugation degree, especially those between the conjugated and unconjugated state, will bring a large spectral variation. To realize such a process, a meso-naked BODIPY (MNBOD) with two electron-withdrawing groups around the core is designed and synthesized. The resulting system is extremely sensitive to bases. The red, highly fluorescent solution readily becomes colorless and non-fluorescent after base addition; however, the color and fluorescence can be totally and instantly restored by addition of acid or formaldehyde. Analyses show that two identical MNBODs are connected by a C-C single bond (sp 3) at the meso-position through a radical reaction that results in an unconjugated, colorless dimer complexed with bases. When the bases are consumed, the dimer immediately dissociates into the red, highly fluorescent, conjugated MNBOD monomer. With 260 nm spectral change and over 120,000 turn-on ratio, this chromophore-reaction can be utilized as a sensitive reaction-based dual-signal probe.
AB - Chromophore reactions with changes to conjugation degree, especially those between the conjugated and unconjugated state, will bring a large spectral variation. To realize such a process, a meso-naked BODIPY (MNBOD) with two electron-withdrawing groups around the core is designed and synthesized. The resulting system is extremely sensitive to bases. The red, highly fluorescent solution readily becomes colorless and non-fluorescent after base addition; however, the color and fluorescence can be totally and instantly restored by addition of acid or formaldehyde. Analyses show that two identical MNBODs are connected by a C-C single bond (sp 3) at the meso-position through a radical reaction that results in an unconjugated, colorless dimer complexed with bases. When the bases are consumed, the dimer immediately dissociates into the red, highly fluorescent, conjugated MNBOD monomer. With 260 nm spectral change and over 120,000 turn-on ratio, this chromophore-reaction can be utilized as a sensitive reaction-based dual-signal probe.
UR - http://www.scopus.com/inward/record.url?scp=85041084297&partnerID=8YFLogxK
U2 - 10.1038/s41467-017-02270-0
DO - 10.1038/s41467-017-02270-0
M3 - Article
C2 - 29367661
AN - SCOPUS:85041084297
SN - 2041-1723
VL - 9
JO - Nature Communications
JF - Nature Communications
IS - 1
M1 - 362
ER -