Synthesis and characterisation of carboxylic acid and diphenylphosphine derivatives in the 1,3-diyne series: Spectral properties of polydiacetylene carboxylates

✍ Scribed by N. M. Agh-Atabay; W. Edward Lindsell; Peter N. Preston; Peter J. Tomb

• Publisher: John Wiley and Sons
• Year: 1993
• Tongue: English
• Weight: 721 KB
• Volume: 31
• Category: Article
• ISSN: 0959-8103
• DOI: 10.1002/pi.4990310410

✦ Synopsis

Abstract

Symmetrically substituted 1,3‐diynes containing hydroxyalkyl (1a‐d), bromoalkyl (1e‐h) (diphenylphosphinyl) (1i‐k) and carboxyalkyl (2a‐d) substituents have been prepared and characterised; the phosphine derivative (1k) has been converted with alkyl iodides (RI; R = Me, Et) into bis(phosphonium) salts (1l and m). During preparation of the diynedioic acid. (2a), the non‐centrosymmetrical diyne, HO~2~CCH~2~CC—CC(CH~2~)~2~OH (3), was also isolated. ^60^Co γ‐Irradiation of diacetylene monomers (2a–d) and 10,12‐tricosadiyn‐1‐oic acid gave the corresponding polydiacetylene derivatives (4a–d and 5), respectively. Rubidium salts of (4c) and (4d), a barium salt of (4c), and a potassium salt of (5) were prepared and isolated; soluble potassium salts of the carboxylic acid polymers (4) were generated in aqueous solution. The effects of changes in pH on the UV/visible absorption spectra of aqueous solutions of selected carboxylic acid polydiacetylenes have been recorded, and are discussed.