title: Development of functionalized cyclotriveratrylene analogues: introduction of withdrawing and π-conjugated groups.
abstract: Cyclotriveratrylene analogues (CTVs) are supramolecular bowl-shaped molecules known for their ability to complex organic and organometallic guests, to form liquid crystals, polymers, or nanostructures. In this Article, we report the synthesis of new cyclotriveratrylene analogues with fluorescence properties in which various electron-withdrawing or π-extended conjugated groups are appended to the wide rim ortho to the methoxy-donating groups. Synthetically, these functionalized CTVs cannot be obtained as CTVs with electron-rich functions by the typical method (i.e., the trimerization of the corresponding benzyl alcohol) but are prepared from a common key intermediate, the C(3)-triiodocyclotriveratrylene (CTV-I(3)), in good yields. Despite the synthetic difficulties encountered due to the presence of three reactive centers, we have demonstrated the possibility of performing Sonogashira coupling and Huisgen cycloaddition reactions directly to the CTV core for the first time. CTVs with π-extended conjugated groups reveal interesting fluorescence profiles. More broadly, this study utilizes CTV-I(3) to introduce novel functionalities into CTVs to keep exploring their potential applications.
authors: Institut des Sciences Moléculaires UMR CNRS 5525, Groupe Nanosystèmes analytiques, Université de Bordeaux, Site ENSCBP, 16 Av. Pey Berland, 33607 Pessac, France.
authors: Lisa
authors: L
authors: Peyrard
authors: Marie-Laurence
authors: ML
authors: Dumartin
authors: Sabine
authors: S
authors: Chierici
authors: Sandra
authors: S
authors: Pinet
authors: Gediminas
authors: G
authors: Jonusauskas
authors: Pierre
authors: P
authors: Meyrand
authors: Isabelle
authors: I
authors: Gosse
mesh_terms: D061565:Cycloaddition Reaction; D004583:Electrons; D005453:Fluorescence; D005456:Fluorescent Dyes / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D011083:Polycyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D017550:Spectroscopy, Fourier Transform Infrared
chemical_list: D005456:Fluorescent Dyes; D011083:Polycyclic Compounds; C483859:cyclotriveratrylene