title: Synthesis and Properties of Heavy Chalcogen Analogues of the Texas Reds and Related Rhodamines.
abstract: Analogues of Texas red incorporating the heavy chalcogens S, Se, and Te atoms in the xanthylium core were prepared from the addition of aryl Grignard reagents to appropriate chalcogenoxanthone precursors. The xanthones were prepared via directed metalation of amide precursors, addition of dichalcogenide electrophiles, and electrophilic cyclization of the resulting chalcogenides with phosphorus oxychloride and triethylamine. The Texas red analogues incorporate two fused julolidine rings containing the rhodamine nitrogen atoms. Analogues containing two "half-julolidine" groups (a trimethyltetrahydroquinoline) and one julolidine and one "half-julolidine" were also prepared. The photophysics of the Texas red analogues were examined. The S-analogues were highly fluorescent, the Se-analogues generated single oxygen (1O2) efficiently upon irradiation, and the Te-analogues were easily oxidized to rhodamines with the telluroxide oxidation state. The tellurorhodamine telluroxides absorb at wavelengths ≥690 nm and emit with fluorescence maxima >720 nm. A mesityl-substituted tellurorhodamine derivative localized in the mitochondria of Colo-26 cells (a murine colon carcinoma cell line) and was oxidizedin vitroto the fluorescent telluroxide.
authors.affiliation: Department of Chemistry, University at Buffalo, The State University of New York , Buffalo, New York 14260-3000, United States.
authors.forename: Mark W
authors.initials: MW
authors.lastname: Kryman
authors.affiliation: Department of Chemistry, University at Buffalo, The State University of New York , Buffalo, New York 14260-3000, United States.
authors.forename: Gregory A
authors.initials: GA
authors.lastname: Schamerhorn
authors.affiliation: Department of Chemistry, University at Buffalo, The State University of New York , Buffalo, New York 14260-3000, United States.
authors.forename: Jacqueline E
authors.initials: JE
authors.lastname: Hill
authors.affiliation: Department of Chemistry, University at Buffalo, The State University of New York , Buffalo, New York 14260-3000, United States.
authors.forename: Brandon D
authors.initials: BD
authors.lastname: Calitree
authors.affiliation: Department of Chemistry, University at Buffalo, The State University of New York , Buffalo, New York 14260-3000, United States.
authors.forename: Kellie S
authors.initials: KS
authors.lastname: Davies
authors.affiliation: Department of Chemistry, University at Buffalo, The State University of New York , Buffalo, New York 14260-3000, United States.
authors.forename: Michelle K
authors.initials: MK
authors.lastname: Linder
authors.affiliation: Institute for Lasers, Photonics and Biophotonics, Department of Chemistry, State University of New York , Buffalo, New York 14260-3000, United States.
authors.forename: Tymish Y
authors.initials: TY
authors.lastname: Ohulchanskyy
authors.affiliation: Department of Chemistry, University at Buffalo, The State University of New York , Buffalo, New York 14260-3000, United States ; Institute for Lasers, Photonics and Biophotonics, Department of Chemistry, State University of New York , Buffalo, New York 14260-3000, United States.
authors.forename: Michael R
authors.initials: MR
authors.lastname: Detty