A new and convenient method for covalent attachment of thioamide groups to the side-walls of carbon nanotubes (SWNT) via the Willgerodt–Kindler (WK) reaction is presented. Treating SWNTs with 4-acetylaniline and subsequently with morpholine as a secondary amine and sulfur leads to the thioamidation of SWNTs. This approach paves the way for a new chemical functionalization protocol to enhance the potential of SWNTs for further chemical reactions applicable in various fields.
This study presents the design and synthetic pathway of unsymmetric ligands based on pyridine-pyrazolate scaffold with Donor–Acceptor (D–A) molecular arrays and their boron complexes to achieve a large Stokes shift. Intermolecular charge transfer (ICT) triggered by the uneven molecular charge distribution from electronically dense pyrazolate (donor) part of the ligands to electron-deficient boron centre (acceptor) resulted in a mega Stokes shift up to 263 nm for selected compounds while retaining the characteristic quantum efficiency and chemical stability. The photophysical properties of derivatization of pyrazolate group in the pyridine-pyrazolate scaffold of diaryl boron complexes were explored based on UV–Visible, steady-state and time-resolved fluorescence spectroscopy. An interesting dual emission along with quenching behaviour was also observed for 2-(6-methoxynaphthelene) 5-(2-pyridyl) pyrazolate boron complex (P5) due to the formation of a twisted intermolecular charge transfer (TICT) state from a locally excited (LE) state rendering it a potential candidate for sensing applications based on H-Bond quenching. In addition, the extended excited state lifetime of the reported compounds compared to classical boron-dipyrromethene (BODIPY) makes them suitable as potential probes for analytical applications requiring a longer excited state lifetime.
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