Polyelectrolytes with Main‐Chain Perylene Units

Abstract

A new soluble polyamine with main chain perylene units is synthesized and subsequently converted into cationic or zwitterionic polyelectrolytes. The optical properties of the monomer 1,6,7,12-tetrakis(4-tert-butylphenoxy)-3,4,9,10-tetra(bromomethyl)perylene and the resulting polymers have been studied with special attention to ongoing de/aggregation processes. UV-Vis and PL spectra of the polymers show a distinct concentration and solvent dependency of the optical properties. In contrast to the corresponding monomer complete deaggregation did not occur for the polymers. The environment-sensitive optical properties should allow applications as sensor materials. The perylene-containing polyelectrolytes may be applied in orthogonal processing schemes toward multilayer electronic devices.

Main-Chain Cationic Polyelectrolytes: Design, Synthesis, and Applications

“…A dipicolinium derivative connected with a spacer can undergo aldol-type coupling to produce cationic polyelectrolytes, where the charges were incorporated before polymerization . Alternatively, a tertiary amine-containing polymer can be synthesized first, and then it can be quaternized in the post-polymerization step to obtain the main-chain cationic polyelectrolytes . Interestingly, besides ammonium- or pyridinium-based non-conjugated main-chain cationic polyelectrolytes, phosphonium-containing main-chain cationic polyelectrolytes are another addition in this category, which can be obtained via substitution polymerization between the diphosphine-containing unit and different benzyl bromides. , …”

“…In 2012, Scherf and co-workers synthesized perylene-based mainchain polyamines and quaternized to zwitterionic or cationic polyelectrolytes. 36 The reaction between tetrabromomethyl compound 15 and ethylenediamine produced polyamine 16, which gave cationic polyelectrolyte P27a and zwitterionic polyelectrolyte P27b upon reacting with MeI and 1,4-butane sultone, respectively (Scheme 20). Both polyelectrolytes P27a and P27b were thermally stable up to 180 °C.…”

“…16 Alternatively, a tertiary amine-containing polymer can be synthesized first, and then it can be quaternized in the postpolymerization step to obtain the main-chain cationic polyelectrolytes. 36 Interestingly, besides ammonium-or pyridinium-based non-conjugated main-chain cationic polyelectrolytes, phosphonium-containing main-chain cationic polyelectrolytes are another addition in this category, which can be obtained via substitution polymerization between the diphosphine-containing unit and different benzyl bromides. 60,61 This class of pyridinium-based non-conjugated polyelectrolytes were utilized in device fabrication as a result of their good film-forming ability and liquid crystalline properties.…”

“…segments. These are derived mainly from polyviologens, 7 viologen-type building blocks, 35 quaternary ammonium-linked perylene units, 36 poly(pyridinium triflates), 37 aromatic ionenes, 38 and chloranil-based units 39 as the charged building blocks (Chart 3). These polyelectrolytes have applications in various fields, such as optoelectronic devices, DNA sensing, solar cells, and water splitting.…”

Cationic Main‐Chain Polyelectrolytes with Pyridinium‐Based p‐Phenylenevinylene Units and Their Aggregation‐Induced Gelation

“…Nonconjugated polyelectrolytes were also generated based on ammonium, pyridinium, or viologen as charged building blocks present either in the main or side chain. Also, nonconjugated polyelectrolytes containing main‐chain perylene units have been reported . Recently, polyelectrolyte‐based dye‐sensitized solar cells were fabricated from conjugated polymers with ammonium iodide side chains, or based on imidazolium iodide‐containing polymeric gel electrolytes as well as 1‐methyl‐3‐hexyl‐imidazolium iodide blended in low molecular mass organogelators …”