Excited-state intermolecular proton transfer dependent on the substitution pattern of anthracene–diurea compounds involved in fluorescent ON1–OFF–ON2 response by the addition of acetate ions

2017 ◽  
Vol 15 (31) ◽  
pp. 6575-6583 ◽  
Author(s):  
Hisato Matsumoto ◽  
Yoshinobu Nishimura ◽  
Tatsuo Arai
Keyword(s):  
Excited State ◽  
Proton Transfer ◽  
Substitution Pattern ◽  
Intermolecular Proton Transfer

Anthracene–diurea compounds exhibit different excited-state intermolecular proton transfer (ESIPT) reactions depending on the pattern of the substituents.

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.

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

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
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