In
this study, we synthesized three novel aromatic imide-based
conjugated donor(D)-σ-acceptor (A) dyad-based polymers showing
different photophysical properties. These D-σ-A dyad-based polymers
(e.g., BDTBT-NI, BDTBT-NDI, and BDTBT-PDI) consist of the same conjugated
donor main chains (benzodithiophene-bithiophene (BDTBT)) and side
chains bearing different imide acceptors (naphthalimide (NI), naphthalene
diimide (NDI), or perylenediimide (PDI)). The photophysical and electrochemical
characteristics of the three polymers were studied using various methods,
including UV–visible absorption, steady-state fluorescence,
and time-resolved fluorescence experiments as well as cyclic voltammetry.
As the acceptor strength of the side chain was increased, photoinduced
electron transfer from the donor backbone to the acceptor side-chain
moiety was found to occur more effectively. Among the three polymers,
BDTBT-PDI was found to be used as an efficient extractor and portable
naked-eye sensing probe for Fe2+ ions; notably, it exhibited
a “turn-on” fluorescence response with a detection limit
at a picomolar concentration. The BDTBT-PDI:Fe2+ complex
was also used for ultrasensitive detection of spermine (with a Stern–Volmer
constant of 6.7 × 106 M–1) in urine
samples and was established as an efficient portable test kit for
the real-time detection of spermine in the vapor released from fermented
food samples. Finally, the “on–off” fluorescence
behavior of BDTBT-PDI in the presence of Fe2+ and spermine
enabled us to develop molecular logic gates using this polymer.