Synthesis of solvatochromic merocyanine dyes and their immobilization to polymers

Abstract

Solvatochromic merocyanine dyes were immobilized onto polymer surfaces and copolymerized with acrylic resins, yielding novel reversibly solvatochromic polymers, which were used as solvent polarity indicators that exhibited different colors in water and alcohols. To generate solvatochromic polymer for solvent polarity indication, two solvatochromic merocyanine dyes containing moieties, which allow their immobilization onto polymer surfaces, or copolymerization with acrylic and vinyl monomers, were sequentially synthesized in four and six steps. Merocyanine dye (E)‐2‐(2‐(1‐(6‐aminohexyl)pyridinium‐4‐yl)vinyl)‐4,6‐dichlorophenolate (AHPVD) was prepared with a terminal aminohexyl group which allowed covalent bonding to activated carboxylated or sulfonated polymeric materials. The dyes were covalently bonded to the polymer surfaces, such as, nylon, polycarbonate, polyethylene terephthalate, and silicone. Solvatochromic merocyanine dye (E)‐2‐(2‐(1‐(6‐acrylamidohexyl)pyridinium‐4‐yl)vinyl)‐4,6‐dichlorophenolate (AAPVD) was synthesized for radical copolymerization with acrylate and vinyl monomers and oligomers. Side‐chain solvatochromic merocyanine‐containing hydrophilic polymers with differential water and alcohol absorption were obtained upon photoinitiated radical copolymerization with specially formulated acrylated resins. © 2016 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2017, 134, 44451.

Association of 5,5′-Dibromo-o-Cresolsulfonphthalein Anions with Dye Cations in Aqueous Solution

“…Such properties have some squaraines, [59][60][61][62] spiropyrans, 63,64 porphyrins, 65,66 carbo-and merocyanines. [67][68][69][70] They are now being fruitfully studied in the processes of self-and heterogeneous association of dyes. But in contrast to similar structures, sulfonphthaleins (see also the structure of QB or QR in Table 1) are not flattened structures (see DBS, Table 1).…”

Highly Fluorescent Merocyanine and Cyanine PMMA Copolymers

“…[31,32] Nordhaus et al immobilized merocyanine dyes onto a polymer surface and following copolymerization with acrylic resins afforded solvatochromic polymers, which were used as solvent polarity indicators. [33] Furthermore, a cyanine dye was successfully incorporated into a copolymer matrix consisting of an anionic sulfoethyl methacrylate and cationic cyanine dye by Wang et al and used as a sensitizer in organic solar cells. [34] Here, we aim to extend on the general concept of covalently linking dyes into polymer matrices and specifically use previously reported polymethine derivatives to develop novel polymerizable merocyanine and cyanine dyes, to obtain novel polymethine dye-labeled polymers.…”

“…Although polymethines show versatile photophysical properties, their incorporation into polymers has remained rare, for example, with merocyanine dyes showing both positive and negative solvatochromism . Nordhaus et al immobilized merocyanine dyes onto a polymer surface and following copolymerization with acrylic resins afforded solvatochromic polymers, which were used as solvent polarity indicators . Furthermore, a cyanine dye was successfully incorporated into a copolymer matrix consisting of an anionic sulfoethyl methacrylate and cationic cyanine dye by Wang et al and used as a sensitizer in organic solar cells …”

Silicas with Covalently Anchored Fluorosolvatochromic Dyes Suitable for Naked-Eye Detection of Colourless Compounds

“…Therefore, novel materials that can transfer the solvatochromic phenomenon to a solid surface are being developed. The published solvatochromic materials include various polymers [11][12][13][14][15][16][17], silicas [18][19][20][21], organosilanes [22,23], resins [10], organic frameworks [24][25][26] and nanomaterials [27][28][29][30][31]. In this work, we focused on preparing solvatochromic silicas, as silica is a common material used in various industrial and research applications owing to its unique properties, such as chemical inertness, high surface area, porosity, and thermal stability [32].…”