title: Siderophore inspired tetra- and octadentate antenna ligands for luminescent Eu(III) and Tb(III) complexes.
abstract: Following the success of the siderophore-inspired 1,2-hydroxypyridonate (HOPO) and 2-hydroxisophthalamide (IAM) chromophores in Eu(III) and Tb(III) luminescence, we designed three new ligands bearing both chromophores. Syntheses of the octadentate ligands 3,4,3-LI-IAM-1,2-HOPO and 3,4,3-LI-1,2-HOPO-IAM, where the chromophores are attached to different positions in the (LI=linear) spermine backbone, are reported in addition to a tetradentate ligand based on 1,5-diaminopentane. The Gd(III) complexes were prepared and revealed localized triplet states typical for the IAM and HOPO chromophores. Photophysical characterization of the Eu(III) and Tb(III) complexes revealed that the chromophores need to reside at a primary amine of the spermine backbone to be efficient in lanthanide excitation. These systems help us to understand the antenna effect in siderophore inspired chromophores and could be potential targets for sensing and biological imaging applications.
authors.affiliation: Chemical Sciences Division, Lawrence Berkeley National Laboratory, Berkeley, CA 94720, United States; Department of Chemistry, University of California, Berkeley, CA 94720, United States.
authors.forename: Lena J
authors.initials: LJ
authors.lastname: Daumann
authors.affiliation: Chemical Sciences Division, Lawrence Berkeley National Laboratory, Berkeley, CA 94720, United States; Department of Chemistry, University of California, Berkeley, CA 94720, United States.
authors.forename: Philipp
authors.initials: P
authors.lastname: Werther
authors.affiliation: Chemical Sciences Division, Lawrence Berkeley National Laboratory, Berkeley, CA 94720, United States; Department of Chemistry, University of California, Berkeley, CA 94720, United States.
authors.forename: Michael J
authors.initials: MJ
authors.lastname: Ziegler
authors.affiliation: Chemical Sciences Division, Lawrence Berkeley National Laboratory, Berkeley, CA 94720, United States; Department of Chemistry, University of California, Berkeley, CA 94720, United States. Electronic address: raymond@socrates.berkeley.edu.
authors.forename: Kenneth N
authors.initials: KN
authors.lastname: Raymond
mesh_terms: D000577:Amides / Q000138:chemical synthesis / Q000737:chemistry*; D040761:Biomimetic Materials; D015374:Biosensing Techniques; D056831:Coordination Complexes / Q000138:chemical synthesis / Q000737:chemistry*; D003959:Diamines / Q000737:chemistry; D005063:Europium / Q000737:chemistry*; D005682:Gadolinium / Q000737:chemistry; D008024:Ligands; D057054:Molecular Imaging; D010795:Phthalic Acids / Q000138:chemical synthesis / Q000737:chemistry*; D011728:Pyridones / Q000138:chemical synthesis / Q000737:chemistry*; D017262:Siderophores / Q000737:chemistry; D013096:Spermine / Q000737:chemistry; D013725:Terbium / Q000737:chemistry*; D013816:Thermodynamics
chemical_list: D000577:Amides; D056831:Coordination Complexes; D003959:Diamines; D008024:Ligands; D010795:Phthalic Acids; D011728:Pyridones; D017262:Siderophores; D013725:Terbium; D013096:Spermine; C022790:bis-(acetyl)diaminopentane; D005063:Europium; D005682:Gadolinium; C546958:1-hydroxy-2(1H)-pyridinone
keywords: Antenna; Europium; Luminescent lanthanides; Siderophore inspired ligands; Terbium