Diketopyrrolopyrrole j-aggregates formed by self-organization with DNA.
Bis(2-thienyl)diketopyrrolopyrrole with two Zn(II)-cyclens (ZnCyc-DPP) was designed and synthesized to evaluate the selective binding of Zn(II)-cyclen with thymine base in single-strand DNA as a tool for the construction of a highly ordered multichromophore system on DNAs. Through UV/Vis titrations, gel filtration chromatography, and circular dichroism spectroscopy, ZnCyc-DPP formed J-type DPP aggregates with oligo-dTn DNAs. The DPP aggregates absorbed on a gold electrode exhibited good photocurrent responses. The present results show that binding Zn(II)-cyclen-chromophore conjugates and thymine bases together is a powerful tool for preparing DNA-templated multichromophoric systems with specific functions.
Department of Materials Science and Chemistry, University of Hyogo, 2167 Shosha, Himeji, Hyogo 671-2280 (Japan), Fax: (+81) 79-267-4928.
Koji
K
Tsuto
Mitsunobu
M
Nakamura
Tadao
T
Takada
Kazushige
K
Yamana
D015374:Biosensing Techniques / Q000379:methods*; D019086:Bridged Bicyclo Compounds, Heterocyclic; D000080027:Cyclams; D004247:DNA / Q000737:chemistry*; D055664:Electrochemical Techniques; D004566:Electrodes; D005456:Fluorescent Dyes / Q000737:chemistry*; D006046:Gold / Q000737:chemistry; D006571:Heterocyclic Compounds / Q000737:chemistry*; D008958:Models, Molecular; D055668:Photochemical Processes; D011758:Pyrroles / Q000737:chemistry*; D019032:Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization; D013941:Thymine / Q000737:chemistry; D015032:Zinc / Q000737:chemistry*
D019086:Bridged Bicyclo Compounds, Heterocyclic; D000080027:Cyclams; D005456:Fluorescent Dyes; D006571:Heterocyclic Compounds; D011758:Pyrroles; D006046:Gold; D004247:DNA; C038072:cyclen; D015032:Zinc; D013941:Thymine
DNA; aggregation; chromophores; dyes/pigments; self-assembly