135926-93-1Relevant articles and documents
Efficient solid-phase synthesis of regioregular head-to-tail-coupled oligo(3-alkylthiophene)s up to a dodecamer
Kirschbaum, Thomas,Briehn, Christoph A.,Baeuerle, Peter
, p. 1211 - 1216 (2000)
Solid-phase synthesis of isomerically pure head-to-tail-coupled (HT) oligo(3-hexylthiophene)s on chloromethylated polystyrene resin has been developed. Using novel sequences of iodination and Suzuki cross-coupling reaction, a series up to a dodecamer has been synthesized in high yield and purity. Removal of the conjugated oligomers from solid support as methyl esters, saponification and decarboxylation to the HT-coupled oligo(3-alkylthiophene)s could be effectively achieved. The Royal Society of Chemistry 2000.
A versatile and efficient strategy to discrete conjugated oligomers
Lawrence, Jimmy,Goto, Eisuke,Ren, Jing M.,McDearmon, Brenden,Kim, Dong Sub,Ochiai, Yuto,Clark, Paul G.,Laitar, David,Higashihara, Tomoya,Hawker, Craig J.
supporting information, p. 13735 - 13739 (2017/11/06)
An efficient and scalable strategy to prepare libraries of discrete conjugated oligomers (D = 1.0) using the combination of controlled polymerization and automated flash chromatography is reported. From this two-step process, a series of discrete conjugated materials from dimers to tetradecamers could be isolated in high yield with excellent structural control. Facile and scalable access to monodisperse libraries of different conjugated oligomers opens pathways to designer mixtures with precise composition and monomer sequence, allowing exquisite control over their physical, optical, and electronic properties.
Solution processed bulk heterojunction solar cells based on A-D-A small molecules with a dihydroindoloindole (DINI) central donor and different acceptor end groups
Sim, Jangkeun,Lee, Hyejeoung,Song, Kihyoung,Biswas, Subhayan,Sharma, Abhishek,Sharma, Ganesh D.,Ko, Jaejung
supporting information, p. 3508 - 3516 (2016/05/19)
Four acceptor-donor-acceptor (A-D-A) small molecules with dihydroindoloindole (DINI) as the central donor unit and different acceptor end groups such as dicyanovinylene (DCV), indenedione (IND), cyanoacrylate (CA) and rhodanine (Rho) linked through bithiophene as the π-linker, DINI-DCV, DINI-IND, DINI-CA and DINI-Rho, were designed and synthesized for the application as donor materials along with PC71BM as an acceptor for solution processed organic bulk heterojunction solar cells. The effect of acceptor end groups on the photovoltaic performance was investigated. The organic solar cells (OSCs) based on as cast DINI-IND showed the highest power conversion efficiency of 3.04%, as cast DINI-CA showed the lowest PCE of 1.63% and the other two exhibit a PCE in between them. These results showed that acceptor end groups affect the overall performance of the cells. The PCE of OSCs has been further improved up to 7.04% and 6.16% employing two-step annealing (TSA) treated DIN-IND:PC71BM (1:2) and DIN-CN:PC71BM (1:2), respectively. The enhancement in the PCE of OSCs with TSA treated active layers is attributed to the better nanophase morphology, the increase in the crystalline nature and light harvesting efficiency and more balanced charge transport and charge collection probability.
Conjugated polymers with repeated sequences of group 16 heterocycles synthesized through catalyst-transfer polycondensation
Tsai, Chia-Hua,Fortney, Andria,Qiu, Yunyan,Gil, Roberto R.,Yaron, David,Kowalewski, Tomasz,Noonan, Kevin J. T.
supporting information, p. 6798 - 6804 (2016/06/14)
Periodic π-conjugated polymers of the group 16 heterocycles (furan, thiophene, and selenophene) were synthesized with controlled chain lengths and relatively low dispersities using catalyst-transfer polycondensation. The optical gap and redox potentials of these copolymers were fine-tuned by altering the heterocycle sequence, and atomic force microscopy revealed nanofibrillar morphologies for all the materials. Grazing incidence wide-angle X-ray scattering of the thiophene-selenophene copolymers indicated that the π-stacking distance increased with incorporation of the larger heteroatom (from ~3.7-4.0 ?), while the lamellar spacing decreased (from ~15.8-15.2 ?). The study also revealed that periodic sequences allow electronic properties to be tuned while retaining nanofibrillar morphologies similar to those observed for poly(3-hexylthiophene).