![N-[(1,2,3,5,6,7-hexahydropyrido[3,2,1-ij]quinolin-9-yl)methylene]-N-methylmethanaminium tetrafluoroborate](/Databaselist/images/loading.webp)
33985-71-6Relevant academic research and scientific papers
Julolidine-based organic dyes with neutral and anion anchoring groups for dye-sensitized solar cells
Bao, Le Quoc,Hai, Nguyen Thi,Lee, Chi Hwan,Thogiti, Suresh,Kim, Jae Hong
, p. 8813 - 8819 (2015)
Two simple organic dyes (J1 and J2) containing julolidine as the electron donor were synthesized. The simple structure of julolidine attached to the cyanoacetic acid group formed two compounds (anion and neutral forms of E-CCVJ), which showed two different efficiencies when applied to dyesensitized solar cells (DSSCs). Overall conversion efficiencies of 0.91% and 1.21% were obtained for DSSCs based on the cyanoacetic acid (J1) and cyanoacetate (J2) derived dyes, respectively. Compared to the cyanoacetic acid terminated dye, the current density, open circuit voltage and conversion efficiency of the solar cells based on cyanoacetate dye were increased by approximately 24%, 8% and 32%, respectively. The electrochemical impedance analysis showed that the better charge transfer of TiO2 (e-) and electron lifetime (τe) for J2 dye as compared with J1. The power conversion efficiency was found to be quite sensitive to small structural changes to the anchoring moiety.
The influence of tetrahydroquinoline rings in dicyanomethylenedihydrofuran (DCDHF) single-molecule fluorophores
Wang, Hui,Lu, Zhikuan,Lord, Samuel J.,Willets, Katherine A.,Bertke, Jeffrey A.,Bunge, Scott D.,Moerner,Twieg, Robert J.
, p. 103 - 114 (2007)
We have synthesized several series of DCDHF fluorophores with the amine donor either acyclic or constrained in one or two tetrahydroquinoline rings. The absorption and the fluorescence emission wavelengths and quantum yields have been determined and correlated with the specific donor structures. Generally, inclusion of the donor in a ring annulated to the benzene or naphthalene aromatic (Ar) π-core results in a bathochromic shift of absorption and emission accompanied by an increase in the quantum yield. Thus, the tetrahydroquinoline donor provides an efficient way to tailor the properties of fluorophores with substituted amines as electron-donating groups.
A selective and sensitive fluorescent albumin probe for the determination of urinary albumin
Wu, Ying-Yi,Yu, Wan-Ting,Hou, Tai-Cheng,Liu, Tao-Kai,Huang, Chi-Ling,Chen, I.-Chia,Tan, Kui-Thong
, p. 11507 - 11510 (2014)
In this communication, we report a simple albumin probe based on a fluorescent molecular rotor for the detection of trace albumin levels in urine. In the presence of albumin, the probe exhibits remarkable 400-fold fluorescence enhancement with high selectivity and sensitivity. The probe was successfully applied in the quantitative detection of urinary albumin.
Julolidine fluorescent molecular rotors as vapour sensing probes in polystyrene films
Martini, Giulio,Martinelli, Elisa,Ruggeri, Giacomo,Galli, Giancarlo,Pucci, Andrea
, p. 47 - 54 (2015)
We introduce a new sensing polymer system for detection of volatile organic compounds (VOCs) based on the optical response of polystyrene (PS) films doped with julolidine fluorescent molecular rotors (FMRs). The julolidine FMRs exhibited viscosity-dependent changes in the fluorescence intensity, that was enhanced when glycerol was added to ethanol solutions and when they were dispersed in PS films. Thus, reduction in medium mobility slowed down internal motions and allowed for a major radiative decay pathway. The FMR/PS films were exposed to several VOCs, and showed a significant decrease in fluorescence emission when exposed to chloroform, whereas a negligible variation in their emission occurred when methanol was utilized. This vapour sensing behaviour was much more evident when a perfluorodecyl chain was linked to the julolidine core being the molecule segregated at the film surface. This responsive behaviour was affected by solvent composition and its reproducible response was easily determined by luminescence experiments.
Dual-mode tunable viscosity sensitivity of a rotor-based fluorescent dye
Zhu, Liang-Liang,Qu, Da-Hui,Zhang, Dong,Chen, Zhao-Fei,Wang, Qiao-Chun,Tian, He
, p. 1254 - 1260 (2010)
The design and fabrication of new type viscosity sensor on molecular scale will enrich the detection means in both physical and life sciences. In this work, a rotor-containing fluorescent dye was prepared, which can reveal a typical viscosity-sensitive behavior due to the environment-induced non-radiative decay. The viscosity-sensitive behavior of this dye could be tunable (locked and activated) in aqueous environment, either with the reversible light-driven trans/cis-photoisomerization of the cyanostilbene moiety, or with the reversible assembly/disassembly process of β-cyclodextrin (β-CD) to the rotor part. Such dual-mode tunable viscosity sensitivity can be well distinguished by fluorescent spectra. A slope method, on double-logarithmic plots of the fluorescent signal to the corresponding environmental viscosity, makes a quantitative estimation to the tunable viscosity sensitivity, featuring the 'Activated' and the 'Locked' state in this molecular-scale viscometer.
Fluorescent polystyrene films for the detection of volatile organic compounds using the twisted intramolecular charge transfer mechanism ?
Borelli, Mirko,Iasilli, Giuseppe,Minei, Pierpaolo,Pucci, Andrea
, (2017)
Thin films of styrene copolymers containing fluorescent molecular rotors were demonstrated to be strongly sensitive to volatile organic compounds (VOCs). Styrene copolymers of 2-[4-vinyl(1,1-biphenyl)-4-yl]-cyanovinyljulolidine (JCBF) were prepared with different P(STY-co-JCBF)(m) compositions (m% = 0.10–1.00) and molecular weights of about 12,000 g/mol. Methanol solutions of JCBF were not emissive due to the formation of the typical twisted intramolecular charge transfer (TICT) state at low viscosity regime, which formation was effectively hampered by adding progressive amounts of glycerol. The sensing performances of the spin-coated copolymer films (thickness of about 4 μm) demonstrated significant vapochromism when exposed to VOCs characterized by high vapour pressure and favourable interaction with the polymer matrix such as tetrahydrofurane (THF), CHCl3 and CH2Cl2. The vapochromic response was also reversible and reproducible after successive exposure cycles, whereas the fluorescence variation scaled linearly with VOC concentration, thus suggesting future applications as VOC optical sensors.
Solvatochromism and intramolecular charge transfer in dialkylamino-substituted halogenated thienyl chalcone analogues
Echevarria, Lorenzo,Fernández-Terán, Ricardo,Hernández, Florencio Eloy,Sucre-Rosales, Estefanía,Urdaneta, Neudo
, (2020/05/29)
Herein, we present the study of two complementary intramolecular charge transfer (ICT) transitions in two sets of dialkylamino-substituted halogenated thienyl chalcones. We demonstrate that while the first (and stronger) ICT takes place from the 4-(dialkylamino)phenyl moiety to the enone, the second ICT involves the thienyl substituent as the donor. The former is evidenced by a robust solvatochromic shift in both absorption and emission spectra, implying a large increase in the dipole moment upon excitation to the lowest excited state. The latter, a short-range ICT process, is confirmed upon photoexcitation of the higher energy bands, and its enhancement by the larger polarizability of the iodine substituent. With the help of (TD)-DFT calculations and the solvatochromic method, we quantified the extent of these effects and set the stage for further developments towards the design of new chalcone-based dyes. We demonstrated that theoretical calculations allow fine-tuning the sensitive balance between these complementary ICT processes.
A fluorescent molecular rotor probe for tracking plasma membranes and exosomes in living cells
Au-Yeung, Sung King,Chen, Qingxin,Feng, Ling,Hailu, Hagos Birhanu,Liu, Zhiyang,Pang, Qiuxiang,Sun, Hongyan,Xie, Yusheng,Yang, Mengsu,Yao, Xi,Zhang, Jie,Zhang, Liang
supporting information, p. 8480 - 8483 (2020/08/13)
A rotor-based probe MRMP-1 was designed and synthesized. MRMP-1 can bind to plasma membranes very quickly and stably with remarkable fluorescence enhancement. It can be used to monitor the dynamic changes in cell membranes in real-time under stimuli conditions. Importantly, MRMP-1 is the first rotor-based fluorescent sensor to label exosomes in living cells.
Novel aza-BODIPY based small molecular NIR-II fluorophores for: In vivo imaging
Bai, Lei,Sun, Pengfei,Liu, Yi,Zhang, Hang,Hu, Wenbo,Zhang, Wansu,Liu, Zhipeng,Fan, Quli,Li, Lin,Huang, Wei
supporting information, p. 10920 - 10923 (2019/09/18)
The development of new NIR-II fluorophores, particularly those with facile syntheses, high fluorescence quantum yields, and stable and tunable photophysical properties, is challenging. Herein, we report a new class of small molecular NIR-II fluorophores based on aza-dipyrromethene boron difluoride (aza-BODIPY) dyes. We demonstrate promising photophysical properties of these dyes, such as large Stokes shift, superior photostability, and good fluorescence brightness as nanoparticles in aqueous solution. Because of these properties and high resolution and deep penetration NIR-II imaging ability, the aza-BODIPY based dyes show great potential as NIR-II imaging agents.
Synthesis, Structure, and Properties of Amino-Substituted Benzhydrylium Ions – A Link between Ordinary Carbocations and Neutral Electrophiles
Mayer, Robert J.,Hampel, Nathalie,Mayer, Peter,Ofial, Armin R.,Mayr, Herbert
supporting information, p. 412 - 421 (2018/09/14)
Optimized synthetic procedures for the straightforward access to eleven amino-substituted diarylmethylium tetrafluoroborates are described. These benzhydrylium ions cover a range of seven orders of magnitude in electrophilicity and provide a link between ordinary carbocations and neutral electrophiles. Five of these highly stabilized benzhydrylium tetrafluoroborates were characterized by single-crystal X-ray crystallography. While the experimentally determined bond lengths and angles in the solid state perfectly agree with those calculated by DFT methods for the gas phase and aqueous solution, crystal packing accounts for large differences in the twist angles of the aryl groups found in the solid state as compared to calculated structures.
