78053-56-2Relevant articles and documents
1,1,4,4-Tetracyanobutadiene-Functionalized Anthracenes: Regioselectivity of Cycloadditions in the Synthesis of Small Near-IR Dyes
Philippe, Clotilde,Bui, Anh Thy,Batsongo-Boulingui, Sabrinah,Pokladek, Ziemowit,Matczyszyn, Katarzyna,Mongin, Olivier,Lemiegre, Loic,Paul, Frederic,Hamlin, Trevor A.,Trolez, Yann
, p. 2007 - 2012 (2021)
Two small 1,1,4,4-tetracyanobutadiene-functionalized chromophores were obtained by careful leverage of the regioselectivity of the cycloaddition reaction of tetracyanoethylene with anthracene-ynamide derivatives, inducing either a [2 + 2] or a [4 + 2] Diels-Alder process. DFT calculations unraveled the mechanism of the [2 + 2] cycloaddition-retroelectrocyclization reaction sequence with ynamides and elucidated the differing mechanisms in the two substrates. The synthesized dyes presented panchromatic absorption extending into the near-IR and far-red/near-IR photoluminescence in the solid state up to 1550 nm.
Efficient diketopyrrolopyrrole-based small-molecule bulk-heterojunction solar cells with different electron-donating end-groups
Kim, Yu Jin,Back, Jang Yeol,Kim, Seul-Ong,Jeon, Chan-Woo,Park, Chan Eon,Kim, Yun-Hi
, p. 2505 - 2513 (2014)
A series of small molecules that contained identical π-spacers (ethyne), a central diketopyrrolopyrrole (DPP) unit, and different aromatic electron-donating end-groups were synthesized and used in organic solar cells (OSCs) to study the effect of electron-donating groups on the device performance. The three compounds, DPP-A-Ph, DPP-A-Na, and DPP-A-An, possessed intense absorption bands that covered a wide range, from 350 to 750 nm, and relatively low HOMO energy levels, from -5.50 to -5.55 eV. DPP-A-An, which contained anthracene end-groups, demonstrated a stronger absorbance and a higher hole mobility than DPP-A-Ph, which contained phenyl groups, and DPP-A-Na, which contained naphthalene units. The power-conversion efficiencies (PCEs) of OSCs based on organic:PC71BM blends (1:1, w/w) with a processed DIO additive were 3.93% for DPP-A-An, 3.02 % for DPP-Na, and 2.26 % for DPP-A-Ph. These findings suggest that a DPP core that is functionalized with electron-donating capping groups constitutes a promising new class of solution-processable small molecules for OSC applications.
Photochemical "Across-a-Ridge" Z-E Isomerization of (Ethenyl-2-d)anthracenes in the Triplet State
Karatsu, Takashi,Misawa, Hiroaki,Nojiri, Mikiko,Nakahigashi, Naoko,Watanabe, Seiichi,et al.
, p. 508 - 512 (2007/10/02)
Deuterated ethenylanthracenes, 1-, 2-, and 9-(ethenyl-(Z)-2-d)anthracene, and 2-(ethenyl-(E)-2-d)anthracene ((Z)-1-, 2-, and 9-EAD, and (E)-2-EAD, respectively) undergo photochemical Z-E isomerization under thermal activation.The temperature dependence of their isomerization quantum yields and the temperature independence of lifetimes of their Tn 1 absorptions indicate that EADs isomerize adiabatically between the Z and E isomers in the lowest excited triplet state by overcoming an activation barrier (Ea = 19-46 kJ mol-1) of the perpendicularly twisted geometry.The activation parameters of isomerization, ΔH (17-42 kJ mol-1) and ΔS (-40 to -113 J K-1 mol-1), decrease in the order of 2-, 1-, and 9-isomers; however, ΔG (50-54 kJ mol-1) is almost constant irrespective of the substitution position of the anthracene nucleus.