title: Highly solvatochromic fluorescent naphthalimides: design, synthesis, photophysical properties and fluorescence switch-on sensing of ct-DNA.
abstract: We report the design, synthesis and photophysical properties of highly solvatochromic donor/acceptor substituted naphthalimide based fluorophores. The synthesized naphthalimides containing propargyl ends showed highly solvatochromic intramolecular charge transfer (ICT) feature as was revealed from the UV-visible, fluorescence photophysical properties of these fluorophores and DFT/TDDFT calculation. Fluorescence life times for the imide fluorophores were also measured in different solvents. The solid state photophysical property of donor substituted naphthalimide 1 showed promising for future application in material sciences. Furthermore, both the donor/acceptor substituted naphthalimide fluorophores 1-2 were exploited in sensing calf-thymus DNA via switch-on fluorescence response. The propargyl linker containing naphthalimides can further be exploited for the synthesis of labeled biomolecular building blocks.
authors.affiliation: Bioorganic Chemistry Laboratory, Department of Chemistry, Indian Institute of Technology Guwahati, Guwahati 781039, India. ssbag75@iitg.ernet.in
authors.forename: Subhendu Sekhar
authors.initials: SS
authors.lastname: Bag
authors.forename: Manoj Kumar
authors.initials: MK
authors.lastname: Pradhan
authors.forename: Rajen
authors.initials: R
authors.lastname: Kundu
authors.forename: Subhashis
authors.initials: S
authors.lastname: Jana
mesh_terms: D000818:Animals; D002417:Cattle; D004247:DNA / Q000737:chemistry* / Q000378:metabolism; D015195:Drug Design; D005456:Fluorescent Dyes / Q000737:chemistry*; D006860:Hydrogen Bonding; D015335:Molecular Probes / Q000737:chemistry; D053644:Naphthalimides / Q000138:chemical synthesis / Q000737:chemistry*; D012997:Solvents / Q000737:chemistry*; D013056:Spectrophotometry, Ultraviolet
chemical_list: D005456:Fluorescent Dyes; D015335:Molecular Probes; D053644:Naphthalimides; D012997:Solvents; D004247:DNA; C427203:calf thymus DNA