Diacetylene-containing polymers XII. Synthesis and characterization of dye-containing poly(hexa-2,4-butadiynylenoxydibenzoates)

Abstract

Several novel diacetylene-containingpolymers containing diacetylenic groups in the main chains and dyes in the side-chains were synthesized using paraand meta-propargyloxybenzoicacids and four azo dyes. The polymers were synthesized by the oxidative coupling polymerization of dyecontaining bisacetylenic monomers, and were characterized and their thermal properties examined. All of the polymers gave thin lms with excellent optical quality by casting or spin coating. They showed T g at around 100 ± C and the diacetylenic groups cross-linked on heating at above 160 ± C. The UV-irradiated spin-coated lms were no longer soluble in the solvent and did not even swell or come off from the substrate, indicating that the lms cross-linked completely.

Langmuir-Blodgett Films of Novel Diacetylene-Containing Polymers with High Second Order Nonlinear Optical Susceptibility

“…The four polymers used in this work, poly(hexa-2,4-diynylene-1,6-dioxydi benzoates) and poly(hexa-2,4-diynylene-1,6-dioxycinnamates), shown in the following structure, were prepared by the methods previously reported [6][7].…”

“…Recently however, the present authors have obtained series of novel polymers containing diacetylene groups in their main chains and polar chromophores as the side groups [5][6][7]. Their general structure is shown in Scheme 1.…”

SECOND-ORDER NONLINEAR OPTICAL SUSCEPTIBILITIES OF POLY[(HEXA-2,4-DIYNYLENE-1,6-DIOXY)DIBENZOATES] CONTAINING AZO CHROMOPHORE DISPERSE RED 19 BY ELECTROABSORPTION SPECTROSCOPY

“…They were prepared by the methods described previously. 12 The polymers had inherent viscosities of 0.3-0.4 dl/g in N -methylpyrrolidone (NMP) at 25 • C. They were fractionated by precipitation technique from NMP/methanol, and low molecular weight portions soluble in chloroform were employed, so that they can be made into films by spin-coating from chloroform solution.…”

The Orientation Stability and UV Irradiation of Poly(hexa‐2,4‐diynilene‐1,6‐dioxy)benzoates and Cinnamates ContainingDisperse Red 19

“…Synthesis of the four polymers of which structures are shown in Scheme 1, were reported previously (7,8). Their films were prepared on an ITO coated glass substrate from their NMP solutions at 808C using a spin-coater equipped with heating gadget, and films with thickness of around 500 nm were prepared.…”

“…Present authors have reported previously series of novel polymers consisting of hexa-2,4-diynylene-1,6-dioxydibenzoates and dicinnamates in the main chains and Disperse Red 19 chromophore in the side chains (7,8), as shown in Scheme 1. The 2-NLO coefficients (d 33 ) of some of these polymers were high being over 250 pm/V (9, 10), and the d 33 depended most significantly on the main chain conformation, the para-polymers showing about 5 times greater d 33 than the corresponding meta-polymers.…”