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The development of novel ladder‐type conjugated molecules is crucial for advancing supramolecular chemistry and material science. In this study, we report a straightforward synthesis of new alternating donor‐acceptor (D‐A) ladder‐type heteroarene, FCDTDPP, and demonstrate its application as photothermal agent for imaging and cancer therapy. FCDTDPP is constructed by vinylene bridge between cyclopentadithiophene (D) and diketopyrrolopyrrole (A) through intramolecular Friedel‐Crafts type reaction. FCDTDPP exhibits unique combination of good molecular planarity, efficient intra/inter‐molecular mixed D‐A interactions, and local aromaticity. These features collectively contribute to its broad and intense absorptions with narrow bandgap in red band of the spectra, coupled with multiple vibrational absorption feature, thereby enhancing non‐radiative decay process and resulting in efficient photothermal conversion property. FCDTDPP and its nanoparticles (NPs) exhibit superior photothermal conversion performance and stability under 660 nm laser irradiation. Moreover, in vitro studies reveal that FCDTDPP NPs possess excellent biocompatibility, low cytotoxicity, and robust photothermal therapeutic efficacy, a finding further corroborated by preliminary in vivo experiments in tumor‐bearing mice. This work charts a novel course for the molecular engineering of organic photothermal conversion systems, propelling relevant research forward.
The development of novel ladder‐type conjugated molecules is crucial for advancing supramolecular chemistry and material science. In this study, we report a straightforward synthesis of new alternating donor‐acceptor (D‐A) ladder‐type heteroarene, FCDTDPP, and demonstrate its application as photothermal agent for imaging and cancer therapy. FCDTDPP is constructed by vinylene bridge between cyclopentadithiophene (D) and diketopyrrolopyrrole (A) through intramolecular Friedel‐Crafts type reaction. FCDTDPP exhibits unique combination of good molecular planarity, efficient intra/inter‐molecular mixed D‐A interactions, and local aromaticity. These features collectively contribute to its broad and intense absorptions with narrow bandgap in red band of the spectra, coupled with multiple vibrational absorption feature, thereby enhancing non‐radiative decay process and resulting in efficient photothermal conversion property. FCDTDPP and its nanoparticles (NPs) exhibit superior photothermal conversion performance and stability under 660 nm laser irradiation. Moreover, in vitro studies reveal that FCDTDPP NPs possess excellent biocompatibility, low cytotoxicity, and robust photothermal therapeutic efficacy, a finding further corroborated by preliminary in vivo experiments in tumor‐bearing mice. This work charts a novel course for the molecular engineering of organic photothermal conversion systems, propelling relevant research forward.
The development of novel ladder‐type conjugated molecules is crucial for advancing supramolecular chemistry and material science. In this study, we report a straightforward synthesis of new alternating donor‐acceptor (D‐A) ladder‐type heteroarene, FCDTDPP, and demonstrate its application as photothermal agent for imaging and cancer therapy. FCDTDPP is constructed by vinylene bridge between cyclopentadithiophene (D) and diketopyrrolopyrrole (A) through intramolecular Friedel‐Crafts type reaction. FCDTDPP exhibits unique combination of good molecular planarity, efficient intra/inter‐molecular mixed D‐A interactions, and local aromaticity. These features collectively contribute to its broad and intense absorptions with narrow bandgap in red band of the spectra, coupled with multiple vibrational absorption feature, thereby enhancing non‐radiative decay process and resulting in efficient photothermal conversion property. FCDTDPP and its nanoparticles (NPs) exhibit superior photothermal conversion performance and stability under 660 nm laser irradiation. Moreover, in vitro studies reveal that FCDTDPP NPs possess excellent biocompatibility, low cytotoxicity, and robust photothermal therapeutic efficacy, a finding further corroborated by preliminary in vivo experiments in tumor‐bearing mice. This work charts a novel course for the molecular engineering of organic photothermal conversion systems, propelling relevant research forward.
Conjugated ladder polymers (cLPs) represent an intriguing class of macromolecules, characterized by their multi‐stranded structure, with continuous fused π‐conjugated rings forming the backbone. Isotope substitution, such as deuteration and carbon‐13 labeling, offers unique approaches to address the significant challenges associated with elucidating the structure and solution phase dynamics of these polymers. For instance, selective deuteration can highlight parts of the polymer by controlling the scattering length density of specific molecular sections, thereby enhancing the contrast for neutron scattering experiments. In this context, deuteration of side‐chains in cLPs represents a promising approach to uncover the elusive polymer physics properties of their backbone. The synthesis of two distinct types of cLPs with perdeuterated side‐chains are reported here. During the synthesis, 13C isotope labeling was also employed to verify the low levels of defects in the synthesized polymers. Demonstrating these synthetic successes lays the foundation for rigorous characterization of the defects, conformation, and dynamics of cLPs.
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