TY  - JOUR
A1  - Wong, Joseph K. -H.
A1  - Ast, Sandra
A1  - Yu, Mingfeng
A1  - Flehr, Roman
A1  - Counsell, Andrew J.
A1  - Turner, Peter
A1  - Crisologo, Patrick
A1  - Todd, Matthew H.
A1  - Rutledge, Peter J.
T1  - Synthesis and Evaluation of 1,8-Disubstituted-Cyclam/Naphthalimide Conjugates as Probes for Metal Ions
JF  - ChemistryOpen : including thesis treasury
N2  - Fluorescent molecular probes for metal ions have a raft of potential applications in chemistry and biomedicine. We report the synthesis and photophysical characterisation of 1,8-disubstituted-cyclam/naphthalimide conjugates and their zinc complexes. An efficient synthesis of 1,8-bis-(2-azidoethyl)cyclam has been developed and used to prepare 1,8-disubstituted triazolyl-cyclam systems, in which the pendant group is connected to triazole C4. UV/Vis and fluorescence emission spectra, zinc binding experiments, fluorescence quantum yield and lifetime measurements and pH titrations of the resultant bis-naphthalimide ligand elucidate a complex pattern of photophysical behaviour. Important differences arise from the inclusion of two fluorophores in the one probe and from the variation of triazole substitution pattern (dye at C4 vs. N1). Introducing a second fluorophore greatly extends fluorescence lifetimes, whereas the altered substitution pattern at the cyclam amines exerts a major influence on fluorescence output and metal binding. Crystal structures of two key zinc complexes evidence variations in triazole coordination that mirror the solution-phase behaviour of these systems.
KW  - chromophores
KW  - click triazoles
KW  - fluorescent probes
KW  - macrocyclic compounds
KW  - photophysics
Y1  - 2016
U6  - https://doi.org/10.1002/open.201600010
SN  - 2191-1363
VL  - 5
SP  - 375
EP  - 385
PB  - Wiley-VCH
CY  - Weinheim
ER  -