849062-17-5Relevant articles and documents
Solution-processable two-dimensional conjugated organic small molecules containing triphenylamine cores for photovoltaic application
Liu, Leijing,Li, Hui,Bian, Ji,Qian, Jingy,Wei, Yingjin,Li, Jiyang,Tian, Wenjing
, p. 5009 - 5017 (2014)
Two solution-processable two-dimensional conjugated organic small molecules based on triphenylamine (TPA) cores, TPA-BT-C8 and TPA-3Th, were designed and synthesized. As to TPA-BT-C8, two arms of the TPA core are symmetrically connected with a thiophene donor group and a benzothiadiazole acceptor group, while the third arm consists of a strong acceptor group of 2-(5,5-dimethylcyclohex-2-en-1-ylidene)malononitrile (DCM) connected through a trans double bond with the TPA core. For TPA-3Th, two arms of its TPA core are composed of only donor group, terthiophene, whereas the third arm consists of an acceptor group of cyano-n-octyl acetate connected through a trans double bond with the TPA core. The investigation indicated that TPA-BT-C8 has a lower energy band gap and wider absorption than TPA-3Th due to the strong intramolecular charge transfer effect in TPA-BT-C8. The two molecules have a deep highest occupied molecular orbital (HOMO) energy level. Bulk heterojunction photovoltaic devices were fabricated using TPA-BT-C8 or TPA-3Th as the donor and (6,6)-phenyl C61-butyric acid methyl ester (PCBM) as the acceptor. All the devices have a high open-circuit voltage (Voc) of about 0.9 eV. Devices based on TPA-BT-C8 have a much higher short circuit current (Jsc) (8.47 mA cm-2) and power conversion efficiency (PCE) (2.26%) than devices based on TPA-3Th (4.32 mA cm-2, 1.21%), resulting from wider solar light absorption of TPA-BT-C8 and better compatibility and film-formation ability of TPA-BT-C8 with PCBM than TPA-3Th. Incident photon-to-electron conversion efficiency (IPCE) spectra also confirmed that TPA-BT-C8 based devices have a wider and red-shifted response range than TPA-3Th based devices, which leads to a higher performance of the former devices.
Terthiophene-perylene diimides: Color tuning via architecture variation
Wonneberger, Henrike,Ma, Chang-Qi,Gatys, Martina A.,Li, Chen,Baì?uerle, Peter,Muì?llen, Klaus
, p. 14343 - 14347 (2010)
N, Na?2-Bisoctylperylene diimides (PDIs) have been functionalized in the 1,7-position with terthiophenes of varying architecture giving three new donor-acceptor (D-A) compounds of the same molecular weight. Different conjugation lengths, arrangements, and connections of the thiophene units within themselves and toward the PDI core have strong effects on the optical, electronic, and photochemical properties of the D-A compounds. Like jigsaw pieces joined together to give different pictures, the terthiophenes are linked to PDIs to achieve different colors. These insights into tuning color and energy levels can open new possibilities for tailoring chromophores to their desired applications, e.g., organic photovoltaics or organic field effect transistore. ? 2010 American Chemical Society.
Photocytotoxicity of Oligothienyl-Functionalized Chelates That Sensitize LnIII Luminescence and Generate 1O2
Johnson, Katherine R.,Lombardi, Vincent C.,de Bettencourt-Dias, Ana
supporting information, p. 12060 - 12066 (2020/08/21)
Three new compounds containing a heptadentate lanthanide (LnIII) ion chelator functionalized with oligothiophenes, nThept(COOH)4 (n=1, 2, or 3), were isolated. Their LnIII complexes not only display the characteristic metal-centered emission in the visible or near-infrared (NIR) but also generate singlet oxygen (1O2). Luminescence efficiencies (?Ln) for [Eu1Thept(COO)4]? and [Eu2Thept(COO)4]? are ?Eu=3 percent and 0.5 percent in TRIS buffer and 33 percent and 3 percent in 95 percent ethanol, respectively. 3Thept(COO)44? does not sensitize EuIII emission due to its low-lying triplet state. Near infra-red (NIR) luminescence is observed for all NIR-emitting LnIII and ligands with efficiencies of ?Yb=0.002 percent, 0.005 percent and 0.04 percent for [YbnThept(COO)4]? (n=1, 2, or 3), and ?Nd=0.0007 percent, 0.002 percent and 0.02 percent for [NdnThept(COO)4]? (n=1, 2, or 3) in TRIS buffer. In 95 percent ethanol, quantum yields of NIR luminescence increase and are ?Yb=0.5 percent, 0.31 percent and 0.05 percent for [YbnThept(COO)4]? (n=1, 2, or 3), and ?Nd=0.40 percent, 0.45 percent and 0.12 percent for [NdnThept(COO)4]? (n=1, 2, or 3). All complexes are capable of generating 1O2 in 95 percent ethanol with ?1Ο2 efficiencies which range from 2 percent to 29 percent. These complexes are toxic to HeLa cells when irradiated with UV light (λexc=365 nm) for two minutes. IC50 values for the LnIII complexes are in the range 15.2–16.2 μm; the most potent compound is [Nd2Thept(COO)4]?. The cell death mechanisms are further explored using an Annexin V—propidium iodide assay which suggests that cell death occurs through both apoptosis and necrosis.
