A photochromic naphthopyran dye activated by the intramolecular hydrogen bond and its photodynamics in the ormosil matrix coating

Abstract

Naphthopyran dyes are one important family of photochromic compounds, and the understanding of the effects of internal and external factors on their functions is crucial to their development. In this study, the intramolecular hydrogen bond and host materials have been demonstrated to be essential to their applications. A novel N-(4-chlorophenyl)-3,3-diphenyl-3H-benzo[f]chromene-5-carboxamide (NPase) dye is designed and synthesized based on the condensation reaction of 1,1-diphenylprop-2-yn-1-ol and N-(4-chlorophenyl)-3-hydroxynaphthalene-2-carboxamide in an acidic solution. Both the X-ray analysis of the NPase single crystal and theoretical calculation are used to investigate the molecular configuration and optical property. After the introduction of an intramolecular hydrogen bond by the substitute in the dye, an unusual coplanar structure is theoretically proposed and experimentally confirmed, which affects the tautomerization energy and bathochromic-shift in absorption characteristics greatly. Our results also confirm that the flexible segment of polymethylsiloxane (PDMS) in the host hybrid coating (PMS-PDMS) materials can accelerate the spectrokinetics of NPase which indicates a faster conversion process.

Molecular photoswitches in aqueous environments

“…429 Additional substituents or scaffold hopping to heteroarenes allows further tuning of the UV-Vis absorption properties. [430][431][432][433] Similarly to chromene, the open form of naphthopyran exists as several isomers, which can be converted into each another photochemically and thermally. Attachment of substituents or bridging between the pyran ring and the naphthalenic core by a fused alkyl chain can assist to direct the equilibrium between the isomers towards one species.…”

N‐([1,1ʹ‐biaryl]‐4‐yl)‐1‐naphthamide‐based scaffolds synthesis, their cheminformatics analyses, and screening as bacterial biofilm inhibitor

“…Naphthamides have a broad range of activities such as antitubercular [2], antimicrobial agents [3], anti‐inflammatory [4], anticancer [5], antioxidant [6], and anti‐HIV [7]. They have a broad scope in industries as naphthalene‐containing polyamides are used as starting material of nanocomposites [8], photochromic dyes [9], chemosensors [10], and agrochemicals [11]. Napthamides investigation and axial chirality studies in either diastereoselective or enantioselective reactions are becoming a topic of great interest in chemistry [12].…”

Study of naphthopyran derivatives: structure and photochromic properties in solution and in polymer film

“…Photochromic molecules have attracted much interest in recent years because of their potential applications in a number of areas, such as ophthalmic lenses, fluorescence, conductivity, magnetism, biomedicine and memory devices (Kitagawa et al, 2019;Sousa et al, 2019;Peng et al, 2019;Sun et al, 2019;Shallcross et al, 2013;Cheng et al, 2018;Tochitsky et al, 2018;Huang et al, 2007;Mukhopadhyay & Moorthy, 2016;Paramonov et al, 2011). Naphthopyrans are one of the most important classes of photochromic compounds and have attracted much research interest owing to their simple structure, high colourability and excellent fatigue resistance (Pinto et al, 2016;Zhang et al, 2014;Fang et al, 2014;Inagaki et al, 2018;Brazevic et al, 2017).…”