A series of linear π conjugated arylene oligomers based on 1,5-naphthalene subunit: synthesis, characterization, and properties

Abstract

Gao (2014) A series of linear π conjugated arylene oligomers based on 1,5-naphthalene subunit: synthesis, characterization, and properties, Designed Monomers and Polymers, 17:7, 684-692, DOI: 10.1080/15685551.2014 A series of novel alkoxy-substituted arylene-ethynylene oligomers based on 1,5-naphthalene subunit have been successfully synthesized by palladium-catalyzed cross-coupling reaction. The solubility, thermal, optical, and electrochemical properties have been investigated in detail. The title compounds are soluble in common organic solvents and emit a blue color both in solution and in the solid state, indicating that these oligomers might serve as potential materials in optoelectronic devices.

Arylene‐Ethynylene Oligomers Based on the Proton Sponge

“…It is well known that organic substrates with an extended π‐conjugated system are widely used for creating electronic and optoelectronic devices cheaper and simpler to manufacture than their silicon and germanium analogues . In this context, in recent decades, increasing interest has been focused on π‐conjugated oligomers consisting of alternating C≡C bonds and aromatic nuclei [general name oligo(arylene‐ethynylene)s or shortly OAEs] as a promising class of semiconductors, chemosensors and various electronic devices . OAEs have several advantages over the related polymers since they are monodisperse and easy to purify.…”

“…(1) in most cases, OAEs with phenyl or substituted phenyl rings were studied , . The presence of alkoxy and ester groups with long‐chain alkyl fragments typically increases the solubility of the material;…”

“…(2) oligomers having three aromatic fragments (trimers) are the most studied. Tetra‐, pentamers and longer oligomers are less examined probably due to lower availability;,…”

“…(3) the influence of the groups in the para positions of the terminal aromatic nuclei and substituents in the internal nuclei on the photophysical properties of the oligomer is intensively studied. [3b], [3k], [5a], [5b], [5c] The introduction of electron‐withdrawing substituents usually leads to an increase in the electron affinity of OAE;…”

“…(4) the synthesis of oligo(arylene‐ethynylene)s containing heterocyclic or aromatic rings other than benzene is also wide spread;[3b], [3i], [3j], [5a], [5b]…”