1295502-53-2Relevant articles and documents
Altering Electronic and Optical Properties of Novel Benzothiadiazole Comprising Homopolymers via π Bridges
Karaman, Cansu Zeytun,G?ker, Seza,Hacio?lu, Serife O.,Haciefendio?lu, Tu?ba,Yildirim, Erol,Toppare, Levent
, (2021/04/23)
Four novel benzo[c][1,2,5]thiadiazole comprising monomers namely 5-fluoro-6-((2-octyldodecyl)oxy)-4,7-di(thiophen-2-yl)benzo[c][1,2,5]thiadiazole (TBTT), 5-fluoro-4,7-bis(4-hexylthiophen-2-yl)-6-((2-octyldodecyl)oxy)benzo[c][1,2,5]thiadiazole (HTBTHT), 5-fluoro-4,7-di(furan-2-yl)-6-((2-octyldodecyl)oxy)benzo- [c][1,2,5]thiadiazole (FBTF), and 5-fluoro-6-((2-octyldodecyl)oxy)-4,7-bis(thieno[3,2-b]thiophen-2-yl)benzo[c][1,2,5]thiadiazole (TTBTTT) were designed, and synthesized successfully via Stille polycondensation reaction. The structural characterizations of the monomers were performed by 1H and 13C NMR spectroscopy and High Resolution Mass Spectroscopy (HRMS). The monomers were then electropolymerized in a three electrode cell system via cyclic voltammetry. The electrochemical, and spectroelectrochemical characterization of the polymers were reported in detail. Besides, theoretical calculations were performed to elucidate observed experimental properties. According to the cyclic voltammogram of the polymers, HOMO and LUMO energy levels were calculated as -5.68 eV/-3.91 eV, -5.71 eV/-3.72 eV, -5.61 eV/-4.04 eV, and -5.51 eV/-3.71 eV and the electronic band gaps were 1.77 eV, 1.99 eV, 1.57 eV, and 1.80 eV for PTBTT, PHTBTHT, PFBTF, and PTTBTTT, respectively.
Chlorination: Vs. fluorination: A study of halogenated benzo [c] [1,2,5]thiadiazole-based organic semiconducting dots for near-infrared cellular imaging
Chao, Pengjie,He, Feng,Lai, Hanjian,Lin, Li,Mo, Daize,Tian, Leilei,Zhang, Qingwen
, p. 7740 - 7748 (2020/06/10)
Red/near-infrared organic dyes are becoming increasingly widespread in biological applications. However, designing these dyes with long-wavelength emission, large Stokes shifts, and high fluorescence quantum efficiency is still a very challenging task. In this work, five donor-acceptor (D-A) red/near-infrared fluorophores based on different chlorinated/fluorinated benzo[c][1,2,5]thiadiazole units are designed and synthesized. The photophysical, theoretical calculations, and electrochemical properties explored in this study have proved that the introducing of chlorine atoms will lead to a lower HOMO level, stronger steric hindrance, and a relatively lower quantum yield in solutions. When the organic dots are fabricated, the chlorinated dots demonstrate much higher fluorescence quantum yield, larger Stokes shift, and better photostability than that of the fluorinated dots. After labeling A549 cells, all the chlorinated/fluorinated dots exhibit high red emission intensities. All these results indicated that the subtle change in the halogen atom of the benzo[c][1,2,5]thiadiazole unit is a unique method to tune the photophysical properties of those materials, and also provides good guidelines to design highly efficient red/near-infrared molecules for cellular imaging applications.
Synthesis, characterization, aggregation-induced emission, solvatochromism and mechanochromism of fluorinated benzothiadiazole bonded to tetraphenylethenes
Yu, Chin-Yang,Hsu, Chia-Chieh,Weng, Hsi-Chen
, p. 12619 - 12627 (2018/04/16)
Compounds consisting of unsubstituted, monofluoro and difluoro substituted benzothiadiazole bonded to two tetraphenylethenes were successfully prepared by palladium catalyzed Suzuki-Miyaura cross-coupling reaction of their corresponding co-monomers. All compounds exhibited aggregation-induced emission characteristics when the water fraction was higher than 60% in the THF/water mixtures. The emission maximum for the three compounds was blue-shifted when the water content reached 90% compared to that in THF solution. The intensity of emission maximum of difluorinated benzothiadiazole linked with two tetraphenylethenes was 2.5 times higher in 90% water compared to those in THF solution. Surprisingly, two liquid crystal phases with two distinct emission colors were observed only for the compound containing difluorinated benzothiadiazole bonded to two tetraphenylethene. All compounds showed remarkable solvatochromic properties in selected solvents with different polarities. The powder XRD results and mechanochromism of the compounds suggested that the solid state structures can change from one form to another by grinding, fuming or annealing processes.