Excited-State Intermolecular Proton Transfer of the Firefly’s Chromophored-Luciferin. 2. Water−Methanol Mixtures†

2010 ◽  
Vol 114 (35) ◽  
pp. 9471-9479 ◽  
Author(s):  
Itay Presiado ◽  
Yuval Erez ◽  
Dan Huppert
Keyword(s):  
Excited State ◽  
Proton Transfer ◽  
Intermolecular Proton Transfer

scholarly journals A Solvent-Mediated Excited-State Intermolecular Proton Transfer Fluorescent Probe for Fe3+ Sensing and Cell Imaging

Molecules ◽  
2022 ◽  
Vol 27 (2) ◽  
pp. 516
Author(s):  
You Qian ◽  
Fuchun Gong ◽  
Jiguang Li ◽  
Pan Ma ◽  
Hanming Zhu ◽  
...  
Keyword(s):  
Excited State ◽  
Proton Transfer ◽  
Fluorescent Probe ◽  
Cell Imaging ◽  
Cyano Group ◽  
Proton Donor ◽  
Cell Permeability ◽  
One Pot ◽  
Intermolecular Proton Transfer ◽  
Synthesis Strategy

Constructing excited-state intermolecular proton transfer (ESIPT-e) fluorophores represents significant challenges due to the harsh requirement of bearing a proton donor-acceptor (D-A) system and their matching proton donating-accepting ability in the same molecule. Herein, we synthesized a new-type ESIPT-e fluorophor (2-APC) using the “four-component one-pot” reaction. By the installing of a cyano-group on pyridine scaffold, the proton donating ability of -NH2 was greatly enhanced, enabling 2-APC to undergo ESIPT-e process. Surprisingly, 2-APC exhibited dual-emissions in protic solvents ethanol and normal fluorescence in aprotic solvents, which is vastly different from that of conventional ESIPT-a dyes. The ESIPT emission can be obviously suppressed by Fe3+ due to the coordination reaction of Fe3+ with the A-D system in 2-APC. From this basis, a highly sensitive and selective method was established using 2-APC as a fluorescent probe, which offers the sensitive detection of Fe3+ ranging from 0 to 13 μM with the detection limit of 7.5 nM. The recovery study of spiked Fe3+ measured by the probe showed satisfactory results (97.2103.4%) with the reasonable RSD ranging from 3.1 to 3.8%. Moreover, 2-APC can also exhibit aggregation-induced effect in poor solvent or solid-state, eliciting strong red fluorescence. 2-APC was also applied to cell-imaging, exhibiting good cell-permeability, biocompatibility and color rendering. This multi-mode emission of 2-APC is significant departure from that of conventional extended p-conjugated systems and ESIPT dyes based on a flat and rigid molecular design. The “one-pot synthesis” strategy for the construction of ESIPT molecules pioneered a new route to achieve tricolor-emissive fluorophores.

A Drastic Red-shift of Tautomer Fluorescence Depending on the Substitution Pattern of Pyrene–Urea Compounds Generated by Excited State Intermolecular Proton Transfer

2018 ◽  
Vol 47 (4) ◽  
pp. 483-486 ◽  
Author(s):  
Hisato Matsumoto ◽  
Kyoko Azuma ◽  
Yoshinobu Nishimura ◽  
Tatsuo Arai
Keyword(s):  
Excited State ◽  
Proton Transfer ◽  
Red Shift ◽  
Substitution Pattern ◽  
Intermolecular Proton Transfer ◽  
Urea Compounds

Excited-state intermolecular proton transfer reaction of 6-hydroxyquinoline in protic polar medium

2002 ◽  
Vol 359 (3-4) ◽  
pp. 314-320 ◽  
Author(s):  
M.S. Mehata ◽  
H.C. Joshi ◽  
H.B. Tripathi
Keyword(s):  
Excited State ◽  
Proton Transfer ◽  
Transfer Reaction ◽  
Proton Transfer Reaction ◽  
Polar Medium ◽  
Intermolecular Proton Transfer

Ultrafast Excited-State Intermolecular Proton Transfer in Indigo Oligomer

2019 ◽  
Vol 123 (30) ◽  
pp. 6463-6471
Author(s):  
Xuemei He ◽  
Fan Yang ◽  
Shuang Li ◽  
Xiaoxiao He ◽  
Anchi Yu ◽  
...  
Keyword(s):  
Excited State ◽  
Proton Transfer ◽  
Intermolecular Proton Transfer

Excited-State Intermolecular Proton Transfer Induced “TURN ON” Fluorescent Chemosensor for Selective Detection of PO43– Anion

2011 ◽  
Vol 9 (4) ◽  
pp. 1430-1434 ◽  
Author(s):  
Chirantan Kar ◽  
Sandeep Kumar Dey ◽  
Gopal Das
Keyword(s):  
Excited State ◽  
Proton Transfer ◽  
Fluorescent Chemosensor ◽  
Selective Detection ◽  
Turn On ◽  
Intermolecular Proton Transfer

Photochemistry of Pheomelanin Building Blocks and Model Chromophores: Excited-State Intra- and Intermolecular Proton Transfer

2014 ◽  
Vol 5 (12) ◽  
pp. 2094-2100 ◽  
Author(s):  
Amal El Nahhas ◽  
Torbjörn Pascher ◽  
Loredana Leone ◽  
Lucia Panzella ◽  
Alessandra Napolitano ◽  
...  
Keyword(s):  
Excited State ◽  
Proton Transfer ◽  
Building Blocks ◽  
Intermolecular Proton Transfer

Ultrafast Excited-State Intermolecular Proton Transfer of Cyanine Fluorochrome Dyes

2011 ◽  
Vol 116 (1) ◽  
pp. 85-92 ◽  
Author(s):  
Naama Karton-Lifshin ◽  
Itay Presiado ◽  
Yuval Erez ◽  
Rinat Gepshtein ◽  
Doron Shabat ◽  
...  
Keyword(s):  
Excited State ◽  
Proton Transfer ◽  
Intermolecular Proton Transfer

Excited-State Intermolecular Proton Transfer of Firefly Luciferin V. Direct Proton Transfer to Fluoride and Other Mild Bases

2011 ◽  
Vol 115 (26) ◽  
pp. 7591-7601 ◽  
Author(s):  
Itay Presiado ◽  
Rinat Gepshtein ◽  
Yuval Erez ◽  
Dan Huppert
Keyword(s):  
Excited State ◽  
Proton Transfer ◽  
Intermolecular Proton Transfer ◽  
Firefly Luciferin

Excited-State Intermolecular Proton Transfer of Firefly Luciferin III. Proton Transfer to a Mild Base

2010 ◽  
Vol 114 (51) ◽  
pp. 13337-13346 ◽  
Author(s):  
Itay Presiado ◽  
Yuval Erez ◽  
Dan Huppert
Keyword(s):  
Excited State ◽  
Proton Transfer ◽  
Intermolecular Proton Transfer ◽  
Firefly Luciferin

Coherent intermolecular proton transfer in the acid–base reaction of excited state pyranine

2017 ◽  
Vol 19 (28) ◽  
pp. 18243-18251 ◽  
Author(s):  
Wooseok Heo ◽  
Nizam Uddin ◽  
Jae Woo Park ◽  
Young Min Rhee ◽  
Cheol Ho Choi ◽  
...  
Keyword(s):  
Excited State ◽  
Proton Transfer ◽  
Acid Base ◽  
Acidic Proton ◽  
Intermolecular Proton Transfer

The acidic proton in pyranine is transferred coherently to acetate through the stretching motion of the whole molecule.

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