In this work, a novel donor-acceptor electrochromic monomer (3HTP), containing a pyrene subunit connected to a quinoxaline acceptor bridge, is synthesized. The corresponding polymer, poly-(3HTP), is directly deposited onto an indium tin oxide (ITO)/glass surface via an electrochemical process. Atomic force microscopy (AFM) images reveal that the electrochemically deposited poly-(3HTP) has a smooth surface due to self-assembly of the planar pyrene subunit. Electrochemical and optical properties are investigated via cyclic voltammetry and UV-vis absorption measurements. The polymer fi lm shows a multielectrochromic feature at both anodic and cathodic regimes. Poly-(3HTP) exhibits a strong near-infrared (NIR) absorption at the oxidized state with an optical contrast of 88% (at 1800 nm), a very fast response time of 0.5 s and fast switching times, and longterm stability. Density functional theory calculations reveal that the molecule has a high planarity, and the NIR absorption arises from a strong intramolecular charge transfer from the polymer backbone to the planar pyrene subunit.
Synthesis of 10,13-Bis(4-hexylthiophen-2-yl)phenanthro[4,5-abc]phenazine (3HTP)10,13-Dibromophenanthro[4,5-abc]phenazine (0.46 g, 1 mmol) and tributylstannyl-3-hexylthiophene (0.96 g, 2.1 mmol) were dissolved in 20 mL toluene, and the solution was purged with Macromol. Chem. Phys. 2015, 216, 829−836 Scheme 1. Synthetic route to 3HTP monomer. Macromol. Chem. Phys. 2015, 216, 829−836NIR region exceeds those of reported such as P(PTQ), [ 40 ] PDBQTh [ 41 ] PDBQEd, [ 41 ] PDEFNQ, [ 42 ] PHTQ, [ 43 ] PHTBQ, [ 24 ] PHTPP, [ 24 ] and PPHED. [ 44 ] Thus, poly-(3HTP) can be used in various NIR region applications.