4546-04-7Relevant articles and documents
Solvent-free luminescent organic liquids
Santhosh Babu, Sukumaran,Aimi, Junko,Ozawa, Hiroaki,Shirahata, Naoto,Saeki, Akinori,Seki, Shu,Ajayaghosh, Ayyappanpillai,Moehwald, Helmuth,Nakanishi, Takashi
, p. 3391 - 3395 (2012)
Illuminating! Isolation of a π-core by covalently attached flexible hydrocarbon chains has been employed to synthesize blue-emitting oligo(p-phenylenevinylene) (OPV) liquids with tunable viscosity and optical properties. A solvent-free, stable, white-light emitting ink/paint, which can be applied onto various surfaces and even onto LEDs, was made by blending of liquid OPVs with emissive solid dopants. Copyright
Organic fluorescent molecule with high solid state luminescent efficiency and protonation stimuli-response
Ma, Suqian,Zhang, Jibo,Chen, Jinlong,Wang, Lijuan,Xu, Bin,Tian, Wenjing
, p. 1418 - 1422 (2013)
A novel organic fluorophor with high solid state luminescent efficiency based on 1,4-bis(2,2-di(pyridin-2-yl)vinyl)benzene (BDP2VB) was designed and synthesized. It emits faintly in solution, but becomes a strong emitter in the aggregate state, demonstrating its aggregation induced emission (AIE) property. According to the crystal structure analysis, J-type aggregation was formed in the packing mode of the molecule, which was demonstrated to be beneficial to gain high fluorescent quantum efficiency in solid state. Additionally, the emission color of BDP2VB can change dramatically in solid state as well as in solution by the protonation stimuli. Copyright
Selective esterification of phosphonic acids
Brodzka, Anna,Koszelewski, Dominik,Ostaszewski, Ryszard,Trzepizur, Damian
, (2021/09/27)
Here, we report straightforward and selective synthetic procedures for mono-and diesteri-fication of phosphonic acids. A series of alkoxy group donors were studied and triethyl orthoacetate was found to be the best reagent as well as a solvent for the performed transformations. An important temperature effect on the reaction course was discovered. Depending on the reaction temperature, mono-or diethyl esters of phosphonic acid were obtained exclusively with decent yields. The sub-strate scope of the proposed methodology was verified on aromatic as well as aliphatic phosphonic acids. The designed method can be successfully applied for small-and large-scale experiments without significant loss of selectivity or reaction yield. Several devoted experiments were performed to give insight into the reaction mechanism. At 30?C, monoesters are formed via an intermediate (1,1-diethoxyethyl ester of phosphonic acid). At higher temperatures, similar intermediate forms give diesters or stable and detectable pyrophosphonates which were also consumed to give diesters.31P NMR spectroscopy was used to assign the structure of pyrophosphonate as well as to monitor the reaction course. No need for additional reagents and good accessibility and straightforward purification are the important aspects of the developed protocols.
Rational self-assembly of polygonal organic microcrystals for shape-dependent multi-directional 2D optical waveguides
Liao, Liang-Sheng,Lv, Qiang,Wang, Xue-Dong,Xu, Chao-Fei,Yan, Chang-Cun,Yu, Yue
supporting information, (2021/12/29)
Micro-nano-level photonic waveguide regulation is essential for future on-chip photonic integrated systems and is still of great challenges. We report a molecular design strategy, changing the position of the methyl substituent makes the arrangement of the three isomer molecules different in their respective crystals. Based on this strategy, three sheet-like crystals with different polygonal morphologies were prepared via solution self-assembly approach. The in-depth optical measurements demonstrated that these three microsheet crystals have different 2D optical waveguide performances related to the shapes. Our work provides a feasible design strategy and material preparation method for realizing precise 2D optical waveguide modulation, which lays the foundation for complex photonic integrated systems in the future.
Linear and Star-Shaped Extended Di- and Tristyrylbenzenes: Synthesis, Characterization and Optical Response to Acid and Metal Ions
Bunz, Uwe H. F.,Freudenberg, Jan,Kotlear, Eugen A.,Kushida, Soh,Maier, Steffen,Rominger, Frank,Zhang, Hao
, (2020/06/17)
Two linear 1,4-distyrylbenzenes and five star-shaped 1,3,5-tristyrylbenzene derivatives (L2a and L2b, Y0–Y3 and YNBu) were synthesized and spectroscopically characterized. The photophysical properties, optical response to acid and metal ions were investigated. Upon backbone extension of linear distyrylbenzenes or the introduction of dibutylanilines, the electronic spectra are redshifted. Incorporation of electron-deficient pyridyl units does not significantly affect the optical properties. Variation of the number of pyridine rings and substitution pattern tune the fluorescence response to acids and metal ions. The novel arenes discriminate Al3+, Mn2+, Fe3+, Fe2+, Cd2+, Ag+ and Hg2+.
Piezochromic Luminescence of Donor–Acceptor Cocrystals: Distinct Responses to Anisotropic Grinding and Isotropic Compression
Liu, Yingjie,Zeng, Qingxin,Zou, Bo,Liu, Yu,Xu, Bin,Tian, Wenjing
supporting information, p. 15670 - 15674 (2018/11/23)
Piezochromic luminescent materials that exhibit distinct luminescence responses to different types of mechanical stresses have been emerging as new kinds of materials which are rarely investigated. Herein, we report a donor–acceptor (D–A) charge-transfer (CT) cocrystal, which shows distinct hypochromatic and bathochromatic shifts upon anisotropic grinding and isotropic compression, respectively. Detailed spectroscopic and structural analyses revealed that the hypochromatic shifted emission under grinding is attributable to a structural reorganization from a loosely segregated-stack to a mixed-stack, while the bathochromatic shifted emission originates from the formation of a tighter packing structure. We present rare evidence of a distinct luminescent response to anisotropic grinding and isotropic compression on the basis of structural rearrangement in a D–A cocrystal, and thus enriches our insight into piezochromic luminescence.
Distyrylbenzene-based segmented conjugated polymers: Synthesis, thin film morphology and chemosensing of hydrophobic and hydrophilic nitroaromatics in aqueous media
Almassio, Marcela F.,Romagnoli, Maria J.,Del Rosso, Pablo G.,Schvval, Ana Belén,Garay, Raúl O.
, p. 167 - 179 (2017/03/02)
Two new segmented conjugated polymers bearing distyrylbenzene chromophoric units and their model compounds were synthesized. The tendency of the model compounds to form H- and J-type aggregates in the amorphous matrix was greatly diminished by the twisted polymeric architecture. Fluorescence anisotropy measurements indicated good exciton mobilities in condensed phase. Fluorescence quenching by nitroaromatic aqueous solutions was fast, complete, selective and reversible pointing to a rapid diffusion of analytes into the films. The quenching response to nitrophenols was superior to that against nitrotoluenes. The increase of the electron-donating capabilities by diethoxy-substitution was detrimental to the amorphous morphology and it did not increase sensitivity to NACs. Quenching efficiencies of polymers were not modified when MeOH was used instead of water. The solubility parameter distances, Ra. indicate that the sensing materials show higher responses when their affinity with the analytes is lower. This observation could help in the designing of fluorescent sensors.
Bis-pyridylethenyl benzene as novel backbone for amyloid-β binding compounds
Nabuurs, Rob J.A.,Kapoerchan, Varsha V.,Metaxas, Athanasios,Hafith, Sarah,de Backer, Maaike,Welling, Mick M.,Jiskoot, Wim,van den Nieuwendijk, Adrianus M.C.H.,Windhorst, Albert D.,Overkleeft, Herman S.,van Buchem, Mark A.,Overhand, Mark,van der Weerd, Louise
, p. 6139 - 6148 (2016/11/30)
Detection of cerebral β-amyloid (Aβ) by targeted contrast agents is of great interest for in vivo diagnosis of Alzheimer's disease (AD). Partly because of their planar structure several bis-styrylbenzenes have been previously reported as potential Aβ imaging agents. However, these compounds are relatively hydrophobic, which likely limits their in vivo potential. Based on their structures, we hypothesized that less hydrophobic bis-pyridylethenylbenzenes may also label amyloid. We synthesized several bis-pyridylethenylbenzenes and tested whether these compounds indeed display improved solubility and lower Log?P values, and studied their fluorescent properties and Aβ binding characteristics. Bis-pyridylethenylbenzenes showed a clear affinity for Aβ plaques on both human and murine AD brain sections. Competitive binding experiments suggested a different binding site than Chrysamine G, a well-known stain for amyloid. With a Log?P value between 3 and 5, most bis-pyridylethenylbenzenes were able to enter the brain and label murine amyloid in vivo with the bis(4-pyridylethenyl)benzenes showing the most favorable characteristics. In conclusion, the presented results suggest that bis-pyridylethenylbenzene may serve as a novel backbone for amyloid imaging agents.
Hydrophilic Conjugated Polymers Prepared by Aqueous Horner-Wadsworth-Emmons Coupling
Page, Zachariah A.,Liu, Yao,Puodziukynaite, Egle,Russell, Thomas P.,Emrick, Todd
, p. 2526 - 2532 (2016/05/19)
The synthesis of hydrophilic conjugated polymers typically relies on organometallic coupling methodologies. Here we present an approach to prepare polar poly(arylene-vinylene)s (PAVs) in water using the Horner-Wadsworth-Emmons (HWE) reaction. The additional preparation of discrete arylene vinylene (AVs) afforded insight into HWE kinetics and regioselectivity. Nine novel PAVs and AVs were synthesized, characterized by UV-vis absorption and ultraviolet photoelectron spectroscopy, and studied for their utility in sensing and photovoltaic applications.
Design of Assembled Systems Based on Conjugated Polyphenylene Derivatives and Carbon Nanohorns
Iglesias, Daniel,Guerra, Javier,Gómez, M. Victoria,Rodríguez, Antonio M.,Prieto, Pilar,Vázquez, Ester,Herrero, M. Antonia
, p. 11643 - 11651 (2016/08/05)
Promising materials have been designed and fully characterised by an effective interaction between versatile platforms such as carbon nanohorns (CNHs) and conjugated molecules based on thiophene derivatives. Easy and non-aggressive methods have been described for the synthesis and purification of the final systems. Oligothiophenephenylvinylene (OTP) systems with different geometries and electron density are coupled to the CNHs. A wide range of characterization techniques have been used to confirm the effective interaction between the donor (OTP) and the acceptor (CNH) systems. These hybrid materials show potential for integration into solar cell devices. Importantly, surface-enhanced Raman spectroscopy (SERS) effects are observed without the presence of any metal surface in the system. Theoretical calculations have been performed to study the optimised geometries of the noncovalent interaction between the surface and the organic molecule. The calculations allow information on the monoelectronic energies of HOMO–LUMO orbitals and band gap of different donor systems to be extracted.
