Highly soluble perylene tetracarboxylic diimides (PDI)‐tetrathiafulvalene (TTF) dyad and TTF‐PDI‐TTF triad

Abstract

magnified imageTwo highly soluble donor‐σ‐acceptor and donor‐σ‐accepter‐σ‐donor type fluorescence switches consisting tetrathiafulvalene (TTF) and 3,4,9,10‐perylene tetracarboxylic diimides (PDI) were synthesized. The structure of the dyad and triad as well as their intermediates was characterized by 1H NMR, 13C NMR MS, elemental analysis. Their fluorescence behavior could be modulated by oxidization and reduction of the TTF unit using either chemical or electrochemical method. J. Heterocyclic Chem., (2009).

Redox‐Enabled, pH‐Disabled Pyrazoline–Ferrocene INHIBIT Logic Gates

“…For example, ferrocene‐pyrene and Ir III ‐ferrocene heterobimetallic dyads have Φ F =0.0174 and Φ F =0.010 in acetonitrile and CH 2 Cl 2 , respectively. Perylene‐3,4:9,10 switches with tetrathiafulvalene are reported to have much higher Φ F values of 0.16 and 0.172, but these were reported in CH 2 Cl 2 and assisted by electrochemistry under anhydrous and oxygen free conditions. With respect to examples in mixed aqueous solution, to the best of our knowledge, our naphthalimide‐based AND logic gate ( Φ F(max) =0.086) is the current state‐of‐the‐art .…”

“…At the 5‐position of the pyrazoline ring, 1 – 3 have a ferrocene (electron donor) moiety connected by a methylene spacer (Figure ), which allows for fluorescence switching based on a PET mechanism . The presence of Fe 3+ as an oxidant renders 1 – 3 as off‐on redox‐fluorescent switches . Intrinsic to the pyrazoline (fluorophore) there is also a highly emissive internal charge transfer (ICT) excited state, which at high proton concentrations results in fluorescence quenching due to protonation of the N2 nitrogen atom (receptor) .…”

“…[16] The presenceo fF e 3 + as an oxidant renders 1-3 as off-on redox-fluorescent switches. [17][18][19][20][21][22][23][24] Intrinsic to the pyrazoline (fluorophore) there is also ah ighly emissive internal charge transfer (ICT) excited state, whicha th igh proton concentrations results in fluorescenceq uenching due to protonation of the N2 nitrogen atom (receptor). [25,26] Indeed, our proof-of-concepte xamples 1-3 are endowed with two fluorescence sensing mechanisms.…”

Photoinduced electron transfer as a design concept for luminescent redox indicators

“…The maximum emission is observed at 571 nm, which produces an orange-coloured emission. 47,48 The maximum peak intensity in CH 2 Cl 2 solution is centred at 545 nm. 41,42 Luminescent Ir(III) complexes have recently been exploited in the development of multi-analyte sensing molecules.…”

The Photostability of Two Optical Materials Based on Perylene Diimide Substituted by Different Aromatic Groups at the Bay Area

“…Perylene diimides derivatives (PDIs) have attracted much attention in various material applications, such as organic transistor, semiconductors, fluorescent solar collectors, organic solar cells, and electrophotographic devices, because of their special physical and chemical properties . Recently, some new perylene diimide materials which are of great interest for photophysics and photochemistry are continually reported . Different properties of perylene diimide mainly depend upon various modification methods.…”