223377-42-2

Upstream product

• 98-03-3 thiophene-2-carbaldehyde 
• 42600-58-8 4-(dimethylamino)-1-(chloromethyl)-benzene 
• 2026-42-8 diethyl thien-2-ylmethylphosphonate 
• 100-10-7 4-dimethylamino-benzaldehyde 
• 34904-03-5 4-(N,N-dimethylamino)benzyltriphenylphosphonium iodide 
• 23259-98-5 2-thienylmethyltriphenylphosphonium bromide 
• 586-77-6 4-bromo-N,N-dimethylaniline 
• 548474-55-1 Trimethyl-((E)-2-thiophen-2-yl-vinyl)-silane 
• 636-72-6 2-thiophenemethanol 

Downstream Products

• 287958-61-6 (E)-5-[2-(4-dimethylaminophenyl)-vinyl]-thiophene-2-carbaldehyde 
• 1088704-61-3 cis-N,N-dimethyl-4-(2-(thiophen-2-yl)vinyl)aniline 
• 1168140-20-2 (E)-2-(5-(4-(dimethylamino)styryl)thiophen-2-yl)ethene-1,1,2-tricarbonitrile 

Relevant academic research and scientific papers

Donor-acceptor molecules containing thiophene chromophore: synthesis, spectroscopic study and electrogenerated chemiluminescence

Donor-acceptor molecules containing thiophene chromophore with remarkably large Stokes shift (>210 nm) have been found to exhibit strong and stable ECL emission via the singlet excited state without the addition of any co-reactant or a second compound.

New uncharged 2-thienostilbene oximes as reactivators of organophosphate-inhibited cholinesterases

The inhibition of acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) by organophosphates (OPs) as nerve agents and pesticides compromises normal cholinergic nerve signal transduction in the peripheral and central nervous systems (CNS) leading to cholinergic crisis. The treatment comprises an antimuscarinic drug and an oxime reactivator of the inhibited enzyme. Oximes in use have quaternary nitrogens, and therefore poorly cross the brain–blood barrier. In this work, we synthesized novel uncharged thienostilbene oximes by the Wittig reaction, converted to aldehydes by Vilsmeier formylation, and transformed to the corresponding uncharged oximes in very high yields. Eight trans,anti-and trans,syn-isomers of oximes were tested as reactivators of nerve-agent-inhibited AChE and BChE. Four derivatives reactivated cyclosarin-inhibited BChE up to 70% in two hours of reactivation, and docking studies confirmed their productive interactions with the active site of cyclosarin-inhibited BChE. Based on the moderate binding affinity of both AChE and BChE for all selected oximes, and in silico evaluated ADME properties regarding lipophilicity and CNS activity, these compounds present a new class of oximes with the potential for further development of CNS-active therapeutics in OP poisoning.

ALPHA-SYNUCLEIN LIGANDS

The present invention generally relates to various compounds that are useful as α-synuclein ligands. The invention further relates to methods of using these compounds and their radiolabeled analogs for the detection of synucleinopathies, including Parkinson's disease (PD).

Rational design of double-check mercury ion chemosensors based on photochromic compounds

A new photochromic compound, S1, containing a trans-cis photoisomerizable unit and a mercury detecting chemosensor unit, has been designed and synthesized. S1 displayed dramatic selectivity for mercury ions over other ions, through fluorescence intensity

Synthesis and properties of NLO chromophores with fine-tuned gradient electronic structures

A novel series of heterocycle-based NLO chromophores based on different combinations of auxiliary donor (i.e., benzene, thiophene and pyrrole) and auxiliary acceptor (i.e., thiazole with different regiochemistries) were designed and synthesized. Due to the different electron-rich and poor nature of the auxiliary donors and acceptors, respectively, the resulting NLO chromophores have systematically varied ground-state electronic structures, as evidenced by the 1H NMR, CV and UV-vis investigations. The nonlinear optical properties of the resulting NLO chromophores were studied by UV-vis spectroscopy, Hyper-Rayleigh scattering (HRS), and semi-empirical computations. All the chromophores have very large molecular hyperpolarizabilities (β1000 nm) in the range of 704-1500 × 10-30 esu (or β0, 318-768 × 10-30 esu), which showed a great sensitivity to the gradient electronic structures. Upon increasing the electron density from benzene to thiophene and to pyrrole, substantial increases in β0 were observed; significantly larger β0 values were also observed for NLO chromophores based on "matched" thiazole (C2 is connected to the acceptor) than those based on "un-matched" thiazole (C5 is connected to the acceptor). TGA investigations showed good thermal stability for the resulting NLO chromophores. However, with the increase of electron density of the auxiliary donor, a decrease in thermal and photochemical stability was observed. It is interesting to note that NLO chromophores based on triarylamine as the donor and thiazole as the auxiliary acceptor exhibited not only high thermal stability but also very large β0 values.

Donor-π-acceptor benzothiazole-derived dyes with an extended heteroaryl-containing conjugated system: synthesis, DFT study and antimicrobial activity

A series of novel derivatives containing an electron-donating N,N-dimethylaminophenyl ring connected to an electron-withdrawing benzothiazole or benzothiazolium moiety via a heteroaryl system (furan, thiophene or N-methylpyrrole) and up to two ethenylene

Excited-state proton transfer and excited-state de-hydrogen bonding of the push-pull styryl system

The excited-state reaction of push-pull styryl system was studied in this work. In the excited state, compounds of 2-StP-NMe2, 2-StQ-NMe 2, 4-StQ-NMe2 and 4-StP-NMe2 possess a sufficiently large acidity change f

Trivalent Boron as an Acceptor in Donor - π - Acceptor-Type Compounds for Single- and Two-Photon Excited Fluorescence

The synthesis, structure, and fluorescence properties of a series of new donor - π - acceptor (D - π - A) type compounds, with a trivalent boron, protected by two mesityl groups, as acceptor, and with various typical donors and different π-conjugated bridges, are reported. All these stable organoboron compounds show intense single-photon excited fluorescence (SPEF) and two-photon excited fluorescence (TPEF) in a wide spectral range from blue to green, with the spectral peak position of the SPEF being basically the same as that of the TPEF. The remarkably strong C-B(mesityl)2 bonding, and the well-conjugated π-system, shown in X-ray crystal structures of two compounds, indicate some charge transfer features of the ground state. Meanwhile, spectral data indicate that the charge transfer from donor to acceptor is greatly enhanced in the excited states. Based on typical structural data and comprehensive spectral data, the following structure - property relationships can be drawn: 1) the moderate arylamino donor can more effectively enhance the SPEF and TPEF intensities than can the strong alkylamino donor; 2) stilbene is a better π-bridge than styrylthiophene for its capability of enhancing and blue-shifting the SPEF and TPEF of the corresponding D - π - A compounds; and 3) when compared to its boron-free precursors and other analogues, -B(mesityl)2 invariably and consistently acts as an effective SPEF and TPEF fluorophore in all this series of organoboron compounds, which may result from its strong π -electron-withdrawing and charge transfer-inducing nature in the ground-state and, more dominantly, in the excited-state. Combining all the above positive structure factors, trans-4′-N,N-diphenylamino-4-dimesitylborylstilbene (compound 3) stands out as the optimized green SPEF and TPEF emitter. This compound exhibits an SPEF quantum yield φ of 0.91 at 522 nm in THF, a TPEF cross-section σ′ that is an order of magnitude larger than that of its boron-free precursor upon excitation by 800 nm femto-second laser pulses, and a two-photon absorption section a of 3.0 × 10-48 cm 4 s. In the blue light region, trans-4′ -N-carbazolyl-4-dimesitylborylstilbene (compound 4) shows significant SPEF and TPEF properties, with φ = 0.79 at 464 nm in THF and a large σ′ value, which is five times that of fluorescein upon excitation by 740 nm femto-second laser pulses.

One-pot palladium-catalyzed highly chemo-, regio-, and stereoselective synthesis of trans-stilbene derivatives. A concise and convenient synthesis of resveratrol

A convenient, efficient and highly chemo-, regio-, and stereoselective one-flask synthetic method is reported for the construction of unsymmetrical (or symmetrical) trans-stilbene derivatives based on two sequential Heck-type reactions using tetraalkylammonium salt-based catalyst systems and vinyltrimethylsilane as double bond equivalents. Resveratrol has thus been concisely synthesized.

Regioselective photoamination of 2-styrylthiophenes with ammonia

Photoinduced electron transfer from the singlet excited state of 2-styrylthiophenes (1a-1f) to p-DCB (p-dicyanobenzene) has been proposed from the negative value of ΔGET (the free energy of the electron transfer) calculated by the Rehm-Weller e