A series of poly(pyridinium salt)s-fluorene main-chain ionic polymers with various organic counterions were synthesized by using ring-transmutation polymerization and metathesis reactions. Their chemical structures were characterized by Fourier Transform Infrared (FTIR), proton (1H), and fluorine 19 (19F) nuclear magnetic resonance (NMR) spectrometers. These polymers showed a number-average molecular weight (Mns) between 96.5 and 107.8 kg/mol and polydispersity index (PDI) in the range of 1.12–1.88. They exhibited fully-grown lyotropic phases in polar protic and aprotic solvents at different critical concentrations. Small-angle X-ray scattering for one polymer example indicates lyotropic structure formation for 60–80% solvent fraction. A lyotropic smectic phase contains 10 nm polymer platelets connected by tie molecules. The structure also incorporates a square packing motif within platelets. Thermal properties of polymers were affected by the size of counterions as determined by differential scanning calorimetry and thermogravimetric analysis measurements. Their ultraviolet-visible (UV-Vis) absorption spectra in different organic solvents were essentially identical, indicating that the closely spaced π-π* transitions occurred in their conjugated polymer structures. In contrast, the emission spectra of polymers exhibited a positive solvatochromism on changing the polarity of solvents. They emitted green lights in both polar and nonpolar organic solvents and showed blue light in the film-states, but their λem peaks were dependent on the size of the counterions. They formed aggregates in polar aprotic and protic solvents with the addition of water (v/v, 0%–90%), and their λem peaks were blue shifted.

A series of extended, symmetric viologen triflimides were synthesized by the metathesis reaction of lithium triflimide with the respective viologen tosyalates in methanol. Their chemical structures were characterized by Fourier Transform Infrared, 1 H and 13 C Nuclear Magnetic Resonance spectroscopy and elemental analysis. Their thermotropic liquid-crystalline (LC) properties were examined by a number of experimental techniques including differential scanning calorimetry, thermogravimetric analysis, polarizing optical microscopy and variable temperature X-ray diffraction. The viologen salts containing alkyl chain of two carbon and three carbon atoms were relatively low melting salts. Those of alkyl chains of four carbon and five carbon atoms formed ionic liquids at 88 and 42 °C, respectively. Those of alkyl chain of nine, ten and eleven carbon atoms were high melting salts as high as 166 °C. Those of higher alkyl chains of sixteen, eighteen and twenty carbon atoms showed thermotropic LC phases forming SmC, SmA and an unidentified smectic (Sm) phases, and showed SmA to isotropic transitions at high temperatures. As expected, all the viologen triflimides had excellent stabilities in the temperature range of 338-365 °C.

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Rhodamines and structurally similar rosamines are some of the most highly utilized tools for molecular imaging experiments. We report a general and high-yielding route to produce 18 examples of rhodamines and rosamines, including tetramethylrhodamine, rhodamine B, and Janelia Fluor 549, from a single xanthone intermediate, 3,6-difluoroxanthone. Spectroscopic studies revealed trends in fluorophore efficiency based on substitution patterns at the 3′-, 6′-, and 9′-positions, providing insights to aid future designs of rhodamines/rosamines.