78053-56-2Relevant academic research and scientific papers
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.
Synthesis, characterization, and transistor applications of new linear small molecules: Naphthyl-ethynyl-anthracene-based small molecules containing different alkyl end group
Song, Hyeng Gun,Kim, Yebyeol,Park, So-Min,An, Tae Kyu,Kwon, Soon-Ki,Park, Chan Eon,Kim, Yun-Hi
, p. 349 - 355 (2016)
A novel small molecule consisting of triple bond-bridged naphthalene-anthracene core was synthesized with either a pentyl or decyl end group. The linear and planar shape of naphthalene-anthracene core allowed herringbone packing pattern with enhanced conjugation length and close molecular packing structure. The film morphology of naphthalene-anthracene based small molecules was also affected by the pentyl and decyl groups. The pentyl substituted molecule exhibited more unified and ordered packing patterns than did the decyl substituted example, which showed at least two polymorphs. The p-type semiconducting properties of the two new molecules were characterized by organic field-effect transistor measurements. In annealed devices at 80 °C, the field-effect mobility of pentyl analogue was 0.045 cm2/(V·s), which was about 3 times higher than the decyl substituted compound.
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.
Synthesis and evaluation of novel 3,4-epoxypiperidines as efficient DNA alkylating agents
Kawada, Yuji,Kodama, Tetsuya,Miyashita, Kazuyuki,Imanishi, Takeshi,Obika, Satoshi
experimental part, p. 1249 - 1265 (2010/10/18)
3,4-Epoxypiperidine derivatives are novel DNA alkylating agents based on an active site of the antitumor antibiotics azinomycins A and B. A 3,4-epoxypiperidine library was constructed containing derivatives with a variety of functional groups at C5 via Huisgen reaction, and DNA cleavage activity was examined. Results revealed a more active derivative than any 3,4-epoxypiperidines previously reported.
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.
