155172-86-4

Upstream product

• 2892-63-9 3,4-Dichlorocyclobut-3-ene-1,2-dione 
• 613-29-6 N-Dibutylaniline 
• 62-53-3 aniline 

Downstream Products

• 155172-87-5 3-hydroxy-4[4-(N,N-dibutylanilino)]cyclobut-3-ene-1,2-dione 

Relevant academic research and scientific papers

Synthesis of novel unsymmetrical squarylium dyes absorbing in the near-infrared region

Novel unsymmetrical squarylium dyes which absorb in the near-infrared region were synthesized by a stepwise procedure via intermediate 4-substituted 3-hydroxycyclobut-3-ene-1,2-diones. By introducing benz[c,d]indoline or benzo[b]pyran moieties at one end

Unsymmetrical squaraines with new linkage manner for high-performance solution-processed small-molecule organic photovoltaic cells

Squaraines are promising donor materials because of their strong and broad absorption band in the visible and near infrared regions which is suitable for application in organic photovoltaic (OPV) cells. Two unsymmetrical squaraines (USQs), namely BIBISQ and TIBISQ, with two electron-donating aryls directly linked to the electron-withdrawing squaric acid core (Y-manner) can act as high performance donor materials for solution-processed bulk-heterojunction (BHJ) OPV cells. Both USQs show ideal low bandgaps (1.47 eV for BIBISQ and 1.39 eV for TIBISQ) with an intense and broad absorption band in the range of 500-900 nm, and relatively low HOMO levels of ～-5.10 eV. The BHJ-OPV device based on both of them simultaneously showed excellent short current density (Jsc) (over 13 mA cm-2), open circuit voltage (Voc) (0.84 V), fill factor (FF) (0.49) and power conversion efficiency (PCE) of over 5% under a blend ratio of USQs:PC71BM = 1:3. These results indicate that the two USQs are quite promising candidates for small molecular (SM) OPV cells and the Y-manner should be a quite successful linking method for USQs.

Aggregation of a Surfactant Squaraine in Langmuir-Blodgett Films, Solids, and Solution

The aggregation of a surfactant squaraine, 4-(N-methyl-N-(carboxypropyl)amino)phenyl-4'-(N,N-dibutylamino)phenylsquaraine (SBA), has been studied in a variety of media, including organic solvents, aqueous cyclodextrin (CD) solutions, vesicles, monolayers,

Photovoltaic Devices Prepared through a Trihydroxy Substitution Strategy on an Unsymmetrical Squaraine Dye

A series of unsymmetrical arene-1,3-squaraine (USQ) derivatives with two, three, or four hydroxy (?OH) substituents, namely, USQ-2-OH, USQ-3-OH, or USQ-4-OH, respectively, were designed and synthesized, and the effect of the number of hydroxy groups on the optoelectronic properties of USQs were investigated. Despite the three compounds having similar UV/Vis absorption and HOMO energy levels, solution-processed bulk-heterojunction (BHJ) small-molecule organic solar cells with USQ-3-OH as electron-donor materials exhibit the highest power conversion efficiency of 6.07 %, which could be mainly attributed to the higher hole mobility and smaller phase separation. It is also noteworthy that the short-circuit current (Jsc) of the USQ-3-OH-based device is as high as 14.95 mA cm?2, which is the highest Jsc values reported for squaraine-based BHJ solar cells to date. The results also indicate that more ?OH substituents on squaraine dyes do not necessarily lead to better photovoltaic performance.

Asymmetrical squaraine cyanine dye probe based on substituted aniline, preparation method and application thereof

The invention belongs to the field of chemical analysis test and specifically relates to an asymmetrical squaraine cyanine dye probe based on substituted aniline as well as a preparation method and an application thereof. The method comprises the followin

Development of asymmetrical near infrared squaraines with large Stokes shift

A new strategy of obtaining large Stokes shift squaraine dyes is reported. Archetypal near infrared squaraines typically have very sharp absorption peaks and small Stokes shifts due to their very rigid ground and excited state molecular structures. TDDFT

Self-assembled near-infrared dye nanoparticles as a selective protein sensor by activation of a dormant fluorophore

Design of selective sensors for a specific analyte in blood serum, which contains a large number of proteins, small molecules, and ions, is important in clinical diagnostics. While metal and polymeric nanoparticle conjugates have been used as sensors, small molecular assemblies have rarely been exploited for the selective sensing of a protein in blood serum. Herein we demonstrate how a nonspecific small molecular fluorescent dye can be empowered to form a selective protein sensor as illustrated with a thiol-sensitive near-IR squaraine ( Sq) dye (λabs= 670 nm, λem= 700 nm). The dye self-assembles to form non fluorescent nanoparticles (Dh = 200 nm) which selectively respond to human serum albumin (HSA) in the presence of other thiol-containing molecules and proteins by triggering a green fluorescence. This selective response of the dye nanoparticles allowed detection and quantification of HSA in blood serum with a sensitivity limit of 3 nM. Notably, the Sq dye in solution state is nonselective and responds to any thiol-containing proteins and small molecules. The sensing mechanism involves HSA specifi c controlled disassembly of the Sq nanoparticles to the molecular dye by a noncovalent binding process and its subsequent reaction with the thiol moiety of the protein, triggering the green emission of a dormant fluorophore present in the dye. This study demonstrates the power of a self-assembled small molecular fluorophore for protein sensing and is a simple chemical tool for the clinical diagnosis of blood serum.

Ultrasound stimulated nucleation and growth of a dye assembly into extended gel nanostructures

A squaraine dye functionalized with a bulky trialkoxy phenyl moiety through a flexible diamide linkage (GA-SQ) capable of undergoing self-assembly has been synthesized and fully characterized. Rapid cooling of a hot solution of GA-SQ to 0 °C results in se

A novel squaraine dye with squaramide as a scaffold and the colorimetric detection of amine

A novel unsymmetrical squaramide-linked squaraine dye (SQ) has been synthesized through squaramide 3 and semisquaraine 6. The molecular structure of SQ has been characterized by 1H NMR, IR and MS. Due to the influence of the hydrogen bond and the solvent effect, SQ exhibits unique spectral properties compared with typical squaraine dyes. For its excellent ability of binding primary amine, SQ is a promising receptor of recognizing primary amine.

A controlled supramolecular approach toward cation-specific chemosensors: Alkaline earth metal ion-driven exciton signaling in squaraine tethered podands

Three different squaraine tethered bichromophoric podands 3a-c with one, two, and three oxygen atoms in the podand chain and an analogous monochromophore 4a were synthesized and characterized. Among these, the bichromophores 3a-c showed high selectivity toward alkaline earth metal cations, particularly to Mg2+ and Ca2+ ions, whereas they were optically silent toward alkali metal ions. From the absorption and emission changes as well as from the Job plots, it is established that Mg2+ ions form 1:1 folded complexes with 3a and 3b whereas Ca2+ ions prefer to form 1:2 sandwich dimers. However, 3c invariably forms weak 1:1 complexes with Mg2+, Ca2+, and Sr2+ ions. The signal output in all of these cases was achieved by the formation of a sharp blue-shifted absorption and strong quenching of the emission of 3a-c. The signal transduction is achieved by the exciton interaction of the face-to-face stacked squaraine chromophores of the cation complex, which is a novel approach of specific cation sensing. The observed cation-induced changes in the optical properties are analogous to those of the "H" aggregates of squaraine dyes. Interestingly, a monochromophore 4a despite its binding, as evident from 1H NMR studies, remained optically silent toward Mg2+ and Ca2+ ions. While the behavior of 4a toward Mg2+ ion is understood, its optical silence toward Ca2+ ion is rationalized to the preferential formation of a "Head-Tail-Tail-Head" arrangement in which exciton coupling is not possible. The present study is different from other known reports on chemosensors in the sense that cation-specific supramolecular host-guest complexation has been exploited for controlling chromophore interaction via cation-steered exciton coupling as the mode of signaling.