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Synthesis, characterization and photophysical properties of meso-indole-boron-dipyrromethene derivatives and their cell imaging and viscosity sensing
摘要： Based on the molecular design and structural modification of boron-dipyrromethene (BODIPY), two new BODIPY derivatives with meso-substituted functional indole moieties were successfully prepared. These new compounds were characterized by NMR, HRMS and FTIR, exhibiting the different UV-vis and PL spectral phenomena because of their varied molecular structures in various solvents and different degrees of negative solvatochromism. Theoretical calculations and CV results show that the substituted NO2 group at 5-position of indole is favorable for increasing the oxidation potential of the molecules, while the NH2 group is the opposite. These two BODIPY derivatives have different sensitivities to pH changes, and can be appropriately applied as cell imaging materials due to their good physical chemical characteristics and excellent biocompatibility. In particular, the fluorescence characteristics of BODIPY derivative with the substituted NH2 group at 5-position of indole show a good solvent viscosity dependence, highlighting its potential application for testing the intracellular viscosity changes of the living cell in disease diagnosis.
关键词： meso-indole boron-dipyrromethene derivatives,photoluminescence,fluorescence characteristics,cell imaging,viscosity sensing
更新于2025-09-23 15:23:52
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Small Band gap Boron Dipyrromethene-Based Conjugated Polymers for All-Polymer Solar Cells: The Effect of Methyl Units
摘要： Naphthalene diimide (NDI)-based conjugated polymers have been widely used as the nonfullerene electron acceptor for all-polymer solar cells (all-PSCs), but their low absorption coefficient in the near-infrared (NIR) region severely limits the light harvesting ability in solar cells and hence lowers their photovoltaic performance. In this work, two narrow band gap donor?acceptor conjugated polymers based on boron dipyrromethene (BODIPY) as the electron-deficient unit were developed as the electron donor to combine with a NDI-polymer acceptor in order to significantly improve the photoresponse in the NIR region. More importantly, we found that methyl substitution on the BODIPY segment played an important role in charge transport in these polymers. When methyl units were attached to the α-position of BODIPY, the polymer PMBBDT exhibited high-lying energy levels, improved crystallinity, and dramatically high hole mobility compared to the polymer PBBDT without methyl substitution. Consequently, the power conversion efficiencies (PCEs) could be enhanced from 0.32% for PBBDT- to 5.8% for PMBBDT-based all-PSCs, and the photoresponse covered from 300 to 900 nm. Our results demonstrate that methyl-substituted BODIPY-based conjugated polymers are promising candidates to solve the NIR absorption issue in NDI polymers and, therefore, can be potentially used to further boost the PCEs of all-PSCs similar with organic solar cells based on NIR-fused ring electron acceptors.
关键词： Boron dipyrromethene,Methyl substitution,Conjugated polymers,Near-infrared absorption,All-polymer solar cells
更新于2025-09-11 14:15:04