The invention belongs to the technical field of
organic synthesis, and particularly discloses a TPA-AN and
pyridine conjugate modified
BODIPY fluorescent probe as well as a preparation method and application thereof. According to the near-
infrared NO-BDP fluorescent probe and the preparation method thereof, the mose site of
BODIPY is directionally modified by TPA-AN,
pyridine is unilaterally modified on the alpha site of a
BODIPY parent
nucleus, an expanded
conjugated system is constructed through
Knoevenagel condensation, and the near-
infrared NO-BDP fluorescent probe is obtained. Wherein the TPA-AN provides a strong
electron supply effect and an intramolecular charge transfer (ICT) channel, and the stereo steric hindrance of a
pyridine ring enables a molecular structure to be twisted into a non-planar configuration, so that pi-pi accumulation is reduced, and an ACQ effect is inhibited. Wherein a TPA-AN group and a BODIPY parent
nucleus have a synergistic coordination effect, so that NO-BDP can sensitively recognize a
phenylalanine dipeptide structural unit in the A beta 42
protein, and then sensitive recognition of the A beta
protein is realized; and a pyridine group is introduced to realize
electron conduction of NO-BDP, so that a D-pi-A structure is formed, more
singlet oxygen is generated, a relatively strong
antibacterial effect is shown, and photodynamic
antibiosis is realized. Finally, multifunctional application is realized through the NO-BDP fluorescent probe.