title: Enhancement of two photon absorption properties and intersystem crossing by charge transfer in pentaaryl boron-dipyrromethene (BODIPY) derivatives.
abstract: Novel BODIPY derivatives containing N,N-diphenylamine, 4-methoxyphenyl, 2,4-dimethoxyphenyl, triphenylamine, and 1-pyrene moieties were designed and synthesized for the first time by employing the palladium-catalyzed Suzuki-Miyaura coupling on pentaaryl boron dipyrromethene compounds. The effect of various moieties and charge transfer on linear and nonlinear optical absorption was investigated. It was found that moieties with strong electron donor properties and long conjugation lengths increase charge transfer and enhance intersystem crossing in the investigated compounds. Besides, the investigated compounds showed strong two photon absorption properties at near infrared wavelengths (800 nm and 900 nm), which is required for two photon photodynamic therapy. Two photon absorption cross section values were found to be 83, 454, 331, 472 and 413 GM for , , , and compounds at 800 nm wavelength, respectively. The highest two-photon absorption cross-section value was obtained for the compound containing a triphenylamine moiety due to its more efficient charge transfer characteristics. Strong two-photon absorption properties in the near infrared region, efficient intersystem crossing and heavy atom free nature of the investigated compounds make them good candidates for two photon photodynamic therapy applications. We believe that this work will be one of the leading studies for two-photon photodynamic therapy applications of pentaaryl BODIPY derivatives.
authors.affiliation: Department of Engineering Physics, Faculty of Engineering, Ankara University, 06100 Beşevler, Ankara, Turkey. yoglu@eng.ankara.edu.tr.
authors.forename: B
authors.initials: B
authors.lastname: Küçüköz
authors.affiliation: Department of Chemistry, Faculty of Science, Ankara University, 06100 Beşevler, Ankara, Turkey. hayvali@science.ankara.edu.tr.
authors.forename: G
authors.initials: G
authors.lastname: Sevinç
authors.affiliation: Department of Engineering Physics, Faculty of Engineering, Ankara University, 06100 Beşevler, Ankara, Turkey. yoglu@eng.ankara.edu.tr.
authors.forename: E
authors.initials: E
authors.lastname: Yildiz
authors.affiliation: Department of Engineering Physics, Faculty of Engineering, Ankara University, 06100 Beşevler, Ankara, Turkey. yoglu@eng.ankara.edu.tr.
authors.forename: A
authors.initials: A
authors.lastname: Karatay
authors.affiliation: Dalian University of Technology, State Key Laboratory of Fine Chemicals, School of Chemical Engineering, E-208 West Campus, 2 Ling-Gong Road, Dalian 116024, P. R. China. zhaojzh@dlut.edu.cn.
authors.forename: F
authors.initials: F
authors.lastname: Zhong
authors.affiliation: Department of Chemistry, Faculty of Science, Ankara University, 06100 Beşevler, Ankara, Turkey. hayvali@science.ankara.edu.tr.
authors.forename: H
authors.initials: H
authors.lastname: Yılmaz
authors.affiliation: Department of Engineering Physics, Faculty of Engineering, Ankara University, 06100 Beşevler, Ankara, Turkey. yoglu@eng.ankara.edu.tr.
authors.forename: Y
authors.initials: Y
authors.lastname: Tutel
authors.affiliation: Department of Chemistry, Faculty of Science, Ankara University, 06100 Beşevler, Ankara, Turkey. hayvali@science.ankara.edu.tr.
authors.forename: M
authors.initials: M
authors.lastname: Hayvalı
authors.affiliation: Dalian University of Technology, State Key Laboratory of Fine Chemicals, School of Chemical Engineering, E-208 West Campus, 2 Ling-Gong Road, Dalian 116024, P. R. China. zhaojzh@dlut.edu.cn.
authors.forename: J
authors.initials: J
authors.lastname: Zhao
authors.affiliation: Department of Engineering Physics, Faculty of Engineering, Ankara University, 06100 Beşevler, Ankara, Turkey. yoglu@eng.ankara.edu.tr.
authors.forename: H G
authors.initials: HG
authors.lastname: Yaglioglu
mesh_terms: D001896:Boron Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D002384:Catalysis; D005456:Fluorescent Dyes / Q000138:chemical synthesis / Q000737:chemistry*; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry; D017785:Photons; D055585:Physical Phenomena; D011789:Quantum Theory; D013050:Spectrometry, Fluorescence; D013053:Spectrophotometry; D013329:Structure-Activity Relationship
chemical_list: C095489:4,4-difluoro-4-bora-3a,4a-diaza-s-indacene; D001896:Boron Compounds; D005456:Fluorescent Dyes; D010165:Palladium