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Nam, Sungho,Hahm, Suk Gyu,Khim, Dongyoon,Kim, Hwajeong,Sajoto, Tissa,Ree, Moonhor,Marder, Seth R.,Anthopoulos, Thomas D.,Bradley, Donal D. C.,Kim, Youngkyoo American Chemical Society 2018 ACS APPLIED MATERIALS & INTERFACES Vol.10 No.15
<P>Three triple bond-conjugated naphthalene diimide (NDI) copolymers, poly{[<I>N</I>,<I>N</I>′-bis(2-R<SUB>1</SUB>)-naphthalene-1,4,5,8-bis(dicarboximide)-2,6-diyl]-<I>alt</I>-[(2,5-bis(2-R<SUB>2</SUB>)-1,4-phenylene)bis(ethyn-2,1-diyl)]} (PNDIR<SUB>1</SUB>-R<SUB>2</SUB>), were synthesized via Sonogashira coupling polymerization with varying alkyl side chains at the nitrogen atoms of the imide ring and 2,5-positions of the 1,4-diethynylbenzene moiety. Considering their identical polymer backbone structures, the side chains were found to have a strong influence on the surface morphology/nanostructure, thus playing a critical role in charge-transporting properties of the three NDI-based copolymers. Among the polymers, the one with an octyldodecyl (OD) chain at the nitrogen atoms of imide ring and a hexadecyloxy (HO) chain at the 2,5-positions of 1,4-diethynylbenzene, P(NDIOD-HO), exhibited the highest electron mobility of 0.016 cm<SUP>2</SUP> V<SUP>-1</SUP> s<SUP>-1</SUP>, as compared to NDI-based copolymers with an ethylhexyl chain at the 2,5-positions of 1,4-diethynylbenzene. The enhanced charge mobility in the P(NDIOD-HO) layers is attributed to the well-aligned nano-fiber-like surface morphology and highly ordered packing structure with a dominant edge-on orientation, thus enabling efficient in-plane charge transport. Our results on the molecular structure-charge transport property relationship in these materials may provide an insight into novel design of n-type conjugated polymers for applications in the organic electronics of the future.</P> [FIG OMISSION]</BR>
Gwon, Donghyeon,Hwang, Heejun,Kim, Hye Kyung,Marder, Seth R.,Chang, Sukbok WILEY‐VCH Verlag 2015 Chemistry Vol.21 No.48
<P><B>Abstract</B></P><P>Described herein is the development of practical routes to 8‐aminoquinolines by using readily installable and easily deprotectable amidating reagents. Two scalable procedures were optimized under Rh<SUP>III</SUP>‐catalyzed conditions: i) the use of pre‐generated chlorocarbamates and ii) a two‐step one‐pot process that directly employs carbamates. Both approaches are highly convenient for the gram‐scale synthesis of 8‐aminoquinolines under mild conditions. Facile deprotection of the synthetically versatile amidating groups was achieved under the Pd‐catalyzed transfer hydrogenation conditions with simultaneous deoxygenation of quinoline <I>N</I>‐oxides, thus yielding 8‐aminoquinolines in excellent overall efficiency.</P>
Song, Seulki,Hill, Rebecca,Choi, Kyoungwon,Wojciechowski, Konrad,Barlow, Stephen,Leisen, Johannes,Snaith, Henry J.,Marder, Seth R.,Park, Taiho unknown 2018 Nano energy Vol.49 No.-
<P><B>Abstract</B></P> <P>We report flexible planar perovskite solar cells with robust electron-transport layers (ETLs) processed at low temperature. A poly(allylamine) (PAA; 0.08 wt%) solution was deposited on a C<SUB>60</SUB> layer and heated at 150 °C for 60 s, resulting in the formation of an insoluble robust C<SUB>60</SUB>–PAA electron-transport layer (ETL) on the flexible substrate. The flexible planar perovskite solar cell with the C<SUB>60</SUB>–PAA ETL exhibited excellent properties with 83% efficiency retention (η = 15.2% without hysteresis) after 600 cycles of bending. This performance is superior to that of the flexible device with a C<SUB>60</SUB> ETL fabricated without the use of PAA (65% efficiency retention; η = 9.8% with some hysteresis).</P> <P><B>Highlights</B></P> <P> <UL> <LI> A modified fullerene-based electron transport layer is proposed for stable flexible perovskite device. </LI> <LI> A poly(allylamine) (PAA; 0.08 wt%) solution was deposited on a C<SUB>60</SUB> layer to form a C<SUB>60</SUB>-PAA. </LI> <LI> C<SUB>60</SUB>–PAA electron-transport layer (ETL) is insoluble in perovskite precursor solution. </LI> <LI> Flexible planar perovskite solar cell with the C<SUB>60</SUB>–PAA ETL exhibited excellent properties with 83% efficiency retention. </LI> </UL> </P> <P><B>Graphical abstract</B></P> <P>[DISPLAY OMISSION]</P>
High‐Performance n‐Channel Thin‐Film Field‐Effect Transistors Based on a Nanowire‐Forming Polymer
Hahm, Suk Gyu,Rho, Yecheol,Jung, Jungwoon,Kim, Se Hyun,Sajoto, Tissa,Kim, Felix S.,Barlow, Stephen,Park, Chan Eon,Jenekhe, Samson A.,Marder, Seth R.,Ree, Moonhor WILEY‐VCH Verlag 2013 Advanced functional materials Vol.23 No.16
<P><B>Abstract</B></P><P>A new electrontransport polymer, poly{[<I>N,N′</I>‐dioctylperylene‐3,4,9,10‐bis(dicarboximide)‐1,7(6)‐diyl]‐<I>alt</I>‐[(2,5‐bis(2‐ethyl‐hexyl)‐1,4‐phenylene)bis(ethyn‐2,1‐diyl]} (PDIC8‐EB), is synthesized. In chloroform, the polymer undergoes self‐assembly, forming a nanowire suspension. The nanowire's optical and electrochemical properties, morphological structure, and field‐effect transistor (FET) characteristics are investigated. Thin films fabricated from a PDIC8‐EB nanowire suspension are composed of ordered nanowires and ordered and amorphous non‐nanowire phases, whereas films prepared from a homogeneous PDIC8‐EB solution consist of only the ordered and amorphous non‐nanowire phases. X‐ray scattering experiments suggest that in both nanowires and ordered phases, the PDIC8 units are laterally stacked in an edge‐on manner with respect to the film plane, with full interdigitation of the octyl chains, and with the polymer backbones preferentially oriented within the film plane. The ordering and orientations are significantly enhanced through thermal annealing at 200 °C under inert conditions. The polymer film with high degree of structural ordering and strong orientation yields a high electron mobility (0.10 ± 0.05 cm<SUP>2</SUP> V<SUP>−1</SUP> s<SUP>−1</SUP>), with a high on/off ratio (3.7 × 10<SUP>6</SUP>), a low threshold voltage (8 V), and negligible hysteresis (0.5 V). This study demonstrates that the polymer in the nanowire suspension provides a suitable material for fabricating the active layers of high‐performance n‐channel FET devices via a solution coating process.</P>
4-N,N-Dimethylamino-4'-N'- Mothy1-stilbazolium tosylate의 수화물
홍형기,윤춘섭,서일환,이진호,최성산,오미란,Hong Hyung-Ki,Yoon Choon Sup,Suh Il-Hwan,Lee Jin-Ho,Choi Sung-San,Oh Mi-Ran,Marder Seth R. Korea Crystallographic Association 1997 韓國結晶學會誌 Vol.8 No.1
표제화합물의 결정구조는 4-N,N-dimethylamino-4'-N'-methyl-stilbazolium, $C_{16}H_{19}N_2$와 tosylate, $C_7H_7SO_3$의 불연속한 이분자체로 구성되어 있다. 4-N,N-dimethylamino-4'-N'-methyl-stilbazolium 분자는 중간에 있는 C=C double bond에서 trans conformation을 가지고 있으며 phenyl 및 pyridyl ring들간의 이면각은 $5.7(2)^{\circ}$을 이루어 전분자는 $0.138(8){\AA}$ 내에서 평면을 이루고 있다. Tosylate 분자들은 거리가 각각 2.855(9) and $2.899(8){\AA}$인 O-H...O 수소결합으로 연결된 이분자체를 나타내고 있다. 이 두 분자간의 가장 가까운 거리는 O(3)와 C(16) 원자간의 $3.10(1){\AA}$이다. The crystal structure of the title compound consists of discrete 4-N,N-dimethylamino-4'-N'-methyl-stilbazolium, $C_{16}H_{19}N_2$, and tosylate, $C_7H_7SO_3$, dimer. The 4-N,N-dimethylamino-4'-N'-methyl-stilbazolium molecule has a trans conformation at the central C=C double bond: the dihedral angle between the phenyl and the pyridyl rings is $5.7(2)^{\circ}$ and the whole molecule is planar within $0.138(8){\AA}$. Tosylate molecules display hydrogen-bonded dimers with the O-H...O distances of 2.855(9) and $2.899(8){\AA}$, respectively. The shortest intermolecular contact is the distance $3.10(1){\AA}$ between O(3) and C(16).