Rational Designing of Anthocyanidins-Directed Near-Infrared Two-Photon Fluorescence Probes
arxiv(2024)
摘要
Recently, two-photon fluorescent probes based on anthocyanidins molecules
have attracted extensive attention due to their outstanding photophysical
properties. However, there are only a few two-photon excited fluorescent probes
that really meet the requirements of relatively long emission wavelengths (>600
nm), large two-photon absorption (TPA) cross sections (300 GM), significant
Stokes shift (>80 nm), and high fluorescence intensity. Herein, the
photophysical properties of a series of anthocyanidins with the same
substituents but different fluorophore skeletons were investigated in detail.
Compared with b-series molecules, a-series molecules with a six-membered ring
in the backbone have a slightly higher reorganization energy. This results in
more energy loss upon light excitation, enabling the reaction products to
detect NTR through a larger Stokes shift. More importantly, there is very
little decrease in fluorescence intensity as the Stokes shift increases. These
features are extremely valuable for high-resolution NTR detection. In light of
this, novel 2a-n (n=1-5) compounds are designed, which are accomplished by
inhibiting the twisted intramolecular charge transfer (TICT) effect through
alkyl cyclization, azetidine ring and extending π conjugation. Among them,
2a-3 gains long emission spectrum (λem=691.42 nm), noticeable TPA cross
section (957.36 GM), and large Stokes shift (110.88 nm), indicating that it
serves as a promising candidate for two-photon fluorescent dyes. It is hoped
that this work will offer some insightful theoretical direction for the
development of novel high performance anthocyanin fluorescent materials.
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