The synthesis of hydrophilic conjugated
polymers typically relies on organometallic coupling methodologies.
Here we present an approach to prepare polar poly(arylene–vinylene)s
(PAVs) in water using the Horner–Wadsworth–Emmons (HWE)
reaction. The additional preparation of discrete arylene vinylene
(AVs) afforded insight into HWE kinetics and regioselectivity. Nine
novel PAVs and AVs were synthesized, characterized by UV–vis
absorption and ultraviolet photoelectron spectroscopy, and studied
for their utility in sensing and photovoltaic applications.