title: The Synthesis, Characterization, Crystal Structure and Photophysical Properties of a New Meso-BODIPY Substituted Phthalonitrile.
abstract: A new highly fluorescent difluoroboradipyrromethene (BODIPY) dye (4) bearing an phthalonitrile group at meso-position of the chromophoric core has been synthesized starting from 4-(4-meso-dipyrromethene-phenoxy)phthalonitrile (3) which was prepared by the oxidation of 4-(2-meso-dipyrromethane-phenoxy)phthalonitrile (2). The structural, electronic and photophysical properties of the prepared dye molecule were investigated. The final product exhibit noticeable spectroscopic properties which were examined by its absorption and fluorescence spectra. The original compounds prepared in the reaction pathway were characterized by the combination of FT-IR, (1)H and (13)C NMR, UV-vis and MS spectral data. It has been calculated; molecular structure, vibrational frequencies, (1)H and (13)C NMR chemical shifts and HOMO and LUMO energies of the title compound by using B3LYP method with 6-311++G(dp) basis set, as well. The final product (4) was obtained as single crystal which crystallized in the triclinic space group P-1 with a = 9.0490 (8) Å, b = 10.5555 (9) Å, c = 11.7650 (9) Å, α = 77.024 (6)°, β = 74.437 (6)°, γ = 65.211 (6)° and Z = 2. The crystal structure has intermolecular C-H···F weak hydrogen bonds. The singlet oxygen generation ability of the dye (4) was also investigated in different solvents to determine of using in photodynamic therapy (PDT).
authors.affiliation: Faculty of Arts and Sciences, Department of Chemistry, Sakarya University, 54187, Sakarya, Turkey.
authors.forename: Pinar
authors.initials: P
authors.lastname: Sen
authors.affiliation: Faculty of Arts and Sciences, Department of Chemistry, Yıldız Technical University, 34210, Esenler, Istanbul, Turkey.
authors.forename: Göknur Yaşa
authors.initials: GY
authors.lastname: Atmaca
authors.affiliation: Faculty of Arts and Sciences, Department of Chemistry, Yıldız Technical University, 34210, Esenler, Istanbul, Turkey.
authors.forename: Ali
authors.initials: A
authors.lastname: Erdoğmuş
authors.affiliation: Faculty of Arts and Sciences, Department of Physics, Samsun Ondokuz Mayıs University, 55139, Samsun, Turkey.
authors.forename: Necmi
authors.initials: N
authors.lastname: Dege
authors.affiliation: Fatih Faculty of Education, Primary Science Education Department, Karadeniz Technical University, 61300, Sogutlu, Akcaabat, Turkey.
authors.forename: Hasan
authors.initials: H
authors.lastname: Genç
authors.affiliation: Faculty of Arts and Sciences, Department of Physics, Sakarya University, 54187, Sakarya, Turkey.
authors.forename: Yusuf
authors.initials: Y
authors.lastname: Atalay
authors.affiliation: Faculty of Arts and Sciences, Department of Chemistry, Sakarya University, 54187, Sakarya, Turkey. szy@sakarya.edu.tr.
authors.forename: S Zeki
authors.initials: SZ
authors.lastname: Yildiz
mesh_terms: D001896:Boron Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D060326:Chemistry Techniques, Synthetic; D004396:Coloring Agents / Q000138:chemical synthesis* / Q000737:chemistry*; D018360:Crystallography, X-Ray; D008958:Models, Molecular; D008968:Molecular Conformation; D009570:Nitriles / Q000737:chemistry*; D055668:Photochemical Processes; D026082:Singlet Oxygen / Q000737:chemistry
chemical_list: C095489:4,4-difluoro-4-bora-3a,4a-diaza-s-indacene; D001896:Boron Compounds; D004396:Coloring Agents; D009570:Nitriles; D026082:Singlet Oxygen
keywords: Bodipy; Crystal structure; Electronic spectra; Fluorescence; Phthalonitrile; Synthesis; photodynamic therapy