Boron‐Locked Starazine – A Soluble and Fluorescent Analogue of Starphene

Feng, Yan; Zhou, Jiadong; Qiu, Honglin; Schnitzlein, Matthias; Hu, Jingtao; Liu, Linlin; Würthner, Frank; Xie, Zengqi

doi:10.1002/chem.202200770

Cited by 4 publications

(2 citation statements)

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“…In this respect, the functionalization of π-conjugated systems with main group elements such as boron is attractive because it offers a means to easily tune the electronic structures and optoelectronic properties . Substitution of carbon–carbon (C–C) covalent bonds with isoelectronic dative B ← N units has emerged as a versatile strategy to adjust the energy levels and band gap of conjugated materials. , In addition, the reversibility of the B ← N dative bonds in such systems is an attractive feature for development of stimuli-responsive materials and molecular switches . However, so far only a limited number of low gap molecules containing B ← N units have been introduced .…”

Section: Introductionmentioning

confidence: 99%

Near-Infrared-Absorbing B–N Lewis Pair-Functionalized Anthracenes: Electronic Structure Tuning, Conformational Isomerism, and Applications in Photothermal Cancer Therapy

et al. 2022

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B–N-fused dianthracenylpyrazine derivatives are synthesized to generate new low gap chromophores. Photophysical and electrochemical, crystal packing, and theoretical studies have been performed. Two energetically similar conformers are identified by density functional theory calculations, showing that the core unit adopts a curved saddle-like shape (x-isomer) or a zig-zag conformation (z-isomer). In the solid state, the z-isomer is prevalent according to an X-ray crystal structure of a C6F5-substituted derivative (4-Pf), but variable-temperature nuclear magnetic resonance studies suggest a dynamic behavior in solution. B–N fusion results in a large decrease of the HOMO–LUMO gap and dramatically lowers the LUMO energy compared to the all-carbon analogues. 4-Pf in particular shows significant absorbance at greater than 700 nm while being almost transparent throughout the visible region. After encapsulation in the biodegradable polymer DSPE-mPEG2000, 4-Pf nanoparticles (4-Pf-NPs) exhibit good water solubility, high photostability, and an excellent photothermal conversion efficiency of ∼41.8%. 4-Pf-NPs are evaluated both in vitro and in vivo as photothermal therapeutic agents. These results uncover B–N Lewis pair functionalization of PAHs as a promising strategy toward new NIR-absorbing materials for photothermal applications.

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Section: Introductionmentioning

confidence: 99%

Near-Infrared-Absorbing B–N Lewis Pair-Functionalized Anthracenes: Electronic Structure Tuning, Conformational Isomerism, and Applications in Photothermal Cancer Therapy

et al. 2022

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“…In comparison to other triangular boron-based complexes, the fluorescence intensity of 8 is comparable to that of boron-cored triazatrinaphthylene (2%) but weaker than that of boron-locked starazine (62%). 16 Such weak photoluminescence should be ascribed to the presence of multiple substituents at the molecular periphery and the twisted molecular structure, which causes enhanced nonradiative deactivation. 16 a The estimated Stokes shift is 160 nm, which is larger than those of similar boron difluoride complexes bearing one (95 nm) or two (111 nm) pyridine–indole units, and comparable to that of triazatrinaphthylene with a boron core (157 nm).…”

Section: Resultsmentioning

confidence: 99%