56128-54-2Relevant academic research and scientific papers
Synthesis and Fluorescence Mechanism of the Aminoimidazolone Analogues of the Green Fluorescent Protein: Towards Advanced Dyes with Enhanced Stokes Shift, Quantum Yield and Two-Photon Absorption
Kovács, Ervin,Cseri, Levente,Jancsó, Attila,Terényi, Ferenc,Fül?p, Anna,Rózsa, Balázs,Galbács, Gábor,Mucsi, Zoltán
, p. 5649 - 5660 (2021/11/11)
Novel small-molecular analogues the green fluorescence protein (GFP) chromophore were synthesised to expand and improve this fluorophore family and to deepen the understanding of their fluorescence mechanism. The introduction of an aminophenyl substituent and the repositioning of the hydroxyl group, to enable strong intramolecular hydrogen bonding, not only enhanced fluorescence emission but also resulted in an increased Stokes shift and a considerable redshift. Experimental and computational results described dual fluorescence involving both excited-state intramolecular proton transfer and internal charge transfer (ESIPT-ICT) mechanisms. Screening of the pH and the solvent medium revealed a complicated equilibrium involving hydrogen bonding, protonation and deprotonation that influences the absorption and emission spectra. Further improvement of the photophysical properties via the systematic variation of dialkylamino substituents at a single position of the chromophore led to a two-orders of magnitude enhancement in the quantum yields. In addition, the novel compounds also have significant two-photon absorption, which widens the possibilities for applications in the field of bioimaging.
DPT-mediated synthesis of 2-aminoimidazolidin-4-ones from thioureas tethered to amides
Bepary, Sukumar,Youn, In Kwon,Lim, Hee-Jong,Lee, Ge Hyeong
supporting information, p. 1876 - 1880 (2014/07/07)
2-Aminoimidazolidin-4-ones have been synthesized by using di-2-pyridyl thiocarbonate (DPT), taking the thioureas tethered to amides as the starting materials. Both the primary amides and secondary amides have been subjected to this cyclization method and
Diversified aminohydantoins from ureas and thioureas tethered to amides
Bepary, Sukumar,Youn, In Kwon,Lim, Hee-Jong,Lee, Ge Hyeong
supporting information; experimental part, p. 2542 - 2548 (2012/06/01)
Intramolecular cyclization of thioureas or ureas tethered to amides afforded 2-iminohydantoins and 2-amino-1H-imidazol-4(5H)-ones in very high yields (87-100%) regardless of the substituent (alkyls or aryls). This reaction proceeds through carbodiimides a
Synthesis of a library of imidazolin-4-ones using poly(ethylene glycol) as soluble support
Li, Hong-Xia,Xie, Chang,Ding, Ming-Wu,Liu, Zu-Ming,Yang, Guang-Fu
, p. 2280 - 2282 (2008/02/10)
A library of imidazolin-4-ones has been synthesized using poly(ethylene glycol) (PEG) as soluble polymer support. The imidazolin-4-ones 6 or 7 were synthesized effectively by reaction of primary amine with PEG-supported carbodiimides 4, which were obtaine
THE FORMATION OF PYRAZINES FROM N-β-KETOIMINOTRIPHENYLPHOSPHORANES; IMINOPHOSPHORANE-MEDIATED SYNTHESES OF 2,2,4,4-TETRAPHENYL-N,N'-BIS(2-PENTANE-3-ON)-CYCLOBUTANE-1,3-DIIMINE; 1,3,4-OXADIAZOLES; 2-AMINO-3,5-DIHYDROIMIDAZOL-4-ONES; AND 2-DIPHENYLMETHYL-1,5-DIHYDROIMIDAZOL-4-ONE
Froeyen, Paul
, p. 283 - 293 (2007/10/02)
The aza-Wittig reaction has been applied to the synthesis of the unstable N-β-keto ketenimine (18), which dimerize spontaneously, forming the very sterically hindered 2,2,4,4-tetraphenyl-N,N'-bis (2-pentane-3-on)-cyclobutane-1,3-diimine (21).Iminophosphoranes (33) and (38) are used for the preparation of some novel 1,5 and 3,5-dihydroimidazol-4-ones (36), (41a-b), (42).N-acylamino iminotriphenylphosphoranes (2a-d) are applied for the syntheses of a series of 1,3,4-oxadiazoles (32).The mechanism of the decomposition of the unstable N-β-keto iminotriphenylphosphoranes (1) into pyrazines and triphenylphosphine oxide has been investigated.Key words: Iminophosphoranes; β-keto carbodiimides; N-β-keto ketenimines; heterocycles.
