17821-75-9Relevant articles and documents
Koopman et al.
, (1968)
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.
Effective design of A-D-A small molecules for high performance organic solar cells via F atom substitution and thiophene bridge
He, Anwang,Qin, Yuancheng,Dai, Weili,Zhou, Dan,Zou, Jianping
supporting information, p. 2263 - 2265 (2019/08/26)
Three novel small molecules with acceptor-donor-acceptor (A-D-A) configuration, SBDT1, SBDT2 and SBDT3, where 4,8-bis(octyloxy)benzo[1,2-b:4,5-b′]dithiophene (BDT) as the electron-donating core connecting to thiophene-substituted benzothiadiazole (BT) as electron-withdrawing are reported. The effects of fluorine atoms on the photophysical properties by introducing different fluorine atoms into the benzothiadiazole unit were investigated. These SBDTs exhibit good thermal stability, excellent panchromatic absorption in solution and film. SBDT2 and SBDT3 with fluorine-substituted BT possess a relatively deeper the highest occupied molecular orbital (HOMO). These A-D-A type molecules were treated as donor and PC71BM as acceptor in bulk heterojunction (BHJ) small-molecule organic solar cells (SMOSCs). Among them, device based on SBDT2 gave the best device performance with a PCE of 5.06% with Jsc of 10.56 mA/cm2, Voc of 0.85 V, fill factor (FF) of 56.4%. These studies indicate that proper incorporation of fluorine atoms is an effective way to increase the efficiency of organic solar cells.