Abstract
In order to improve the poor film-forming ability of polymeric ladderphane, di-block copolymers containing perylene diimide (PDI)-linked double-stranded poly(1,6–heptadiyne) ladderphane and branched alkyl side chains modified single-stranded poly(1,6–heptadiyne) were synthesized by metathesis cyclopolymerization (MCP) using Grubbs third-generation catalyst (Ru–III) in tetrahydrofuran solvent. The first block containing the ladderphane structure leads to higher thermal-stability, wider UV–vis absorption, lower LUMO level and ladderphane-induced rigidity and poor film-forming ability. The second block containing long alkyl chains is crucial for the guarantee of excellent film-forming ability. By comparing the effect of ladderphane structure on the resulted copolymers, single-stranded poly(1,6–heptadiyne) derivatives with PDI pedant were also processed. The structures of copolymers were proved by 1H NMR and gel permeation chromatography, electrochemical, photophysical, and thermal-stability performance were achieved by cyclic voltammetry (CV), UV-visible spectroscopy and thermogravimetric analysis (TGA) measurements. According to the experiment results, both copolymers possessed outstanding film-forming ability, which cannot be realized by small PDI molecules and oligomers. And they can serve as a superior candidate as for n-type materials, especially for their relatively wide range of light absorption (λ = 200~800 nm), and lower LUMO level (−4.3 and −4.0 eV).
Highlights
It is well-known that perylene diimide (PDI) chromophores are widely used for constructing n-type organic semiconductors, as PDI derivatives generally show high thermal and chemical stabilities, good electron-accepting abilities, and excellent electron mobilities [1,2,3,4,5]
Great progress has been made on a new class of polymers, which was defined as polymeric ladderphane comprising of double stranded polymeric skeleton with multilayer planar oligoaryl
Diblock copolymer ladderphane containing PDI group was successfully synthesized via metathesis cyclopolymerization (MCP) reaction
Summary
It is well-known that perylene diimide (PDI) chromophores are widely used for constructing n-type organic semiconductors, as PDI derivatives generally show high thermal and chemical stabilities, good electron-accepting abilities, and excellent electron mobilities [1,2,3,4,5]. The superior light-absorbing strength of PDIs in the visible range can be extended to 400-600 nm, depending on the electron-donating or electron-accepting substitutes on the bay positions. Most PDI molecules possess strong crystallizability, which will lead to wide phase separations, reduced exciton diffusion/separation efficiencies, and low power conversion efficiency of the organic solar cells [6]. Great progress has been made on a new class of polymers, which was defined as polymeric ladderphane comprising of double stranded polymeric skeleton with multilayer planar oligoaryl.
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