Revisiting molecularly conformation-planarized organic dyes for NIR-II fluorescence imaging

Abstract

Fluorescence imaging in the second window (NIR-II, 1000–1700 nm) provides deeper penetration depth and higher resolution, but there is still a dilemma for designing NIR-II dyes for simultaneously enhancing fluorescence efficiency and prolonging excitation wavelength. Herein, a molecular conformation planarization strategy has been revisited to guide the synthesis of two donor–acceptor–donor dyes (named T-BBT and BT-BBT). On the one hand, conformational planarization can extend the absorption peaks of T-BBT and BT-BBT to the NIR region with high molar extinction coefficients of 30.5 × 10³ and 16.4 × 10³ L (mol⁻¹ cm⁻¹) at 1064 nm, respectively. On the other hand, structural rigidity can weaken electronic vibration coupling-related non-radiative decay pathways, whereby both T-BBT and BT-BBT display rather high fluorescence efficiencies of 3.6% and 13.5% in solution. Furthermore, a molecular doping strategy is adopted to alleviate fluorescence quenching in the aggregated state by suppressing long-distance energy migration, and 2.5 wt% doped BT-BBT nanoparticles show a high fluorescence efficiency of 2.0%, which enables the application of in vivo deep NIR-II fluorescence imaging for vessels and tumors with high resolution under 980 nm excitation. This work demonstrates that organic dyes with structural planarization can bridge the gap between NIR-II absorption and fluorescence efficiency.