The gram-scale polymerization of a novel azaborine vinyl monomer is reported. We describe an efficient and high-yielding synthesis of B-vinyl-2,1-borazanaphthalene. Homopolymers and co-polymers with 2-vinylnaphthalene are characterized by heteronuclear NMR and absorbance spectroscopy.

The bioorthogonal nature of perfluorocarbons provides a unique platform for introducing dynamic nano-and microdroplets into cells and organisms. To monitor the localization and deformation of the droplets, fluorous soluble fluorophores that are compatible with standard fluorescent protein markers and applicable to cells, tissues, and small organisms are necessary. Here, we introduce fluorous cyanine dyes that represent the most red-shifted fluorous soluble fluorophores to date. We study the effect of covalently appended fluorous tags on the cyanine scaffold and evaluate the changes in photophysical properties imparted by the fluorous phase. Ultimately, we showcase the utility of the fluorous soluble pentamethine cyanine dye for tracking the localization of perfluorocarbon nanoemulsions in macrophage cells and for measurements of mechanical forces in multicellular spheroids and zebrafish embryonic tissues. These studies demonstrate that the red shifted cyanine dyes offer spectral flexibility in multiplexed imaging experiments and enhanced precision in force measurements.

BN 2-vinylnaphthalene (BN2VN) is a novel precursor to vinyl alcohol copolymers via sodium hydroperoxide oxidation. We show that the unusual aromaticity of the BN heterocycle leads to styrene-like reactivity. Computational data including structural parameters and nucleus independent chemical shift (NICS) values support the aromaticity of the BN naphthalene side chain of BN2VN. Styrene (St) and BN2VN reactivity ratios (r 1 (BN2VN) = 0.423; r 2 (St) = 2.30; r 1 r 2 = 0.97) were determined by nonlinear leastsquares (NLLS) statistical methods. We demonstrate control of copolymer physical properties, including glass transition temperature. This work outlines design principles for the synthesis of tailored polymeric styrene−vinyl alcohol architectures.

BN 2-vinylnaphthalene, a BN aromatic vinyl monomer, is copolymerized with styrene under free radical conditions. Oxidation yields styrene-vinyl alcohol (SVA) statistical copolymers with tunable hydroxy group content. Comprehensive spectroscopic investigation provides proof of structure. Physical properties that vary systematically with hydroxy content include solubility and glass transition temperature. BN aromatic polymers represent a platform for the preparation of diverse functional polymeric architectures via the remarkable reaction chemistry of C-B bonds.

Extended azaborine heterocycles are promising biomedical and electronic materials. Herein we report the synthesis of a novel family of azaborine anthracene derivatives and their structural, electrochemical and spectroscopic characterization. We observe that the properties of these materials are remarkably similar to the parent hydrocarbons, suggesting the innocence of the CC to BN bond substitution. Our results support the prospective stability to long-term usage of extended azaborines and the feasibility of using such materials in device applications.