Brynna J. Laughlin

Naphthoxaphospholes as examples of fluorescent phospha-acenes

Seven new fluorescent 2-R-naphtho[2,3-d]oxaphospholes (R-NOPs) (4a–g; R = tBu (a), Ad (b), C(6)H(5) (c), 4-MeC(6)H(4) (d), 4-ClC(6)H(4) (e), 4-BrC(6)H(4) (f ), 4-MeOC(6)H(4) (g)), have been synthesized by cyclocondensation reactions of benzimidoyl chlorides with 3-phosphino-2-naphthol (3). The compounds were characterized by multinuclear NMR, UV-vis, and fluorescence spectroscopy. Compounds 4a–d and 4g were characterized by cyclic voltammetry experiments. The solid state structures of compounds 4b and 4d were also determined by single-crystal X-ray diffraction experiments.

Synthesis, photophysical and electrochemical properties of conjugated polymers incorporating 9,9-dialkyl-1,4-fluorenylene units with thiophene, carbazole and triarylamine comonomers

Three new poly(p-phenylenevinylene) derivatives were synthesized via the Horner–Wittig condensation polymerization. The new polymers (P3–P5) incorporate recently developed 9,9-dihexyl-1,4-fluorenylene repeat units copolymerized with three different functional groups that are of interest for optoelectronic applications of organic semiconducting polymers (triphenylamine (P3), thiophene (P4) and carbazole (P5). The electrochemical properties were probed via cyclic voltammetry and differential pulse voltammetry for new polymers P3–P5, as well as previously reported but not electrochemically characterized poly(p-phenylene vinylene) derivatives P1 and P2. The electronic absorption and photoluminescence properties of all five 1,4-fluorenylene-containing copolymers were characterized in solution and were compared to other poly(p-phenylenevinylene) copolymers with similar functional groups.