Synthesis and Properties of Conjugated Poly(Aryleneethynylene)S

Ultrafast excited-state dynamics of phenyleneethynylene oligomers in solution

“…Reaction products were separated by flash chromatography (FC) on Merck silica gel 60 (0.040-0.063 mm, 230-400 mesh), except otherwise noted. 1 H NMR: Bruker Avance DPX360 ( 1 H 300.14 MHz), or Bruker Avance DRX500 ( 1 H 500.13 MHz) in CDCl 3 solutions unless otherwise stated, chemical shifts ( ) are given in parts per million relative to Si(CH 3 ) 4 as internal standard, and J values are in hertz. Assignments are based on homonuclear COSY-45, 1 H{ 1 H} NOE difference correlations, and/or chemical shifts.…”

Supramolecular Organization of Foldable Phenylene Ethynylene Oligomers

“…Solvent-dependent effects were also observed in 1 H NMR experiments [23]. In acetonitrile, upfield shifting of aromatic resonances was observed for the longer length oligomers (6)(7)(8)(9), which is attributed to the p-stacking of aromatic units. However, negligible shifting of aromatic resonances was observed in chloroform [23,24].…”

“…A series of oligo mPEs (1)(2)(3)(4)(5)(6)(7)(8)(9) were substituted with triethylene glycol monomethyl ether (Tg) side chains, which impart solubility in a wide range of organic solvents [23]. The side chains were attached through an ester linkage making the aromatic groups electron deficient, enhancing the propensity of the backbone to undergo p-p stacking [24].…”

“…Because of this, para-phenylene ethynylenes (pPE)s will not be covered in this review. However, there are several excellent reviews of pPE synthesis, structure, and function in the recent literature that discuss the intermolecular order of those systems [7][8][9][10][11][12][13][14][15]. Similarly, phenylene ethynylene macrocycles, which form a wide range of supramolecular aggregates with interesting stacking behavior, will not be covered but have been extensively reviewed [16][17][18][19][20][21][22].…”

Poly(aryleneethynylene)s

“…PAEs are like rigid rods and are poorly soluble [15] unless flexible side chains are present to entropically drive solubility. Alternatively, ionic or hydrogen-bonding groups that exhibit strong enthalpic interactions with solvent (e.g., water) can also be used.…”