145543-83-5Relevant articles and documents
Effect of molecular weight on electronic, electrochemical and spectroelectrochemical properties of poly(3,3″-dioctyl-2,2′5′, 2″-terthiophene)
Pokrop, Rafal,Verilhac, Jean-Marie,Gasior, Anna,Wielgus, Ireneusz,Zagorska, Malgorzata,Travers, Jean-Pierre,Pron, Adam
, p. 3099 - 3106 (2006)
Poly(3,3″-dioctyl-2,2′5′,2″-terthiophene), obtained from its corresponding monomer by oxidative polymerization with FeCl 3, has been fractionated into five fractions of reduced polydispersity, covering the Mn range from 1.50 kDa to 10.50 kDa (measured vs. polystyrene standards). The effect of Mn on spectroscopic, electrochemical, spectroelectrochemical and electrical transport properties has been investigated. Fractions of growing Mn show an increasing bathochromic shift of the band originating from the π-π* transition in the neutral polymer with the appearance of a clear vibrational structure for the two highest molecular fractions. The onset of oxidative doping determined from the cyclic voltammogram shifts towards lower potentials with increasing molecular weight. A similar trend is observed for doping induced near infrared bands, which shift towards lower energies (higher wavelengths) with increasing molecular weight and appear at lower potentials in spectroelectrochemical experiments. Finally, a comparison of the FET mobility in two transistors fabricated under identical conditions from polymer fractions differing in their molecular weight shows that a ca. fourfold increase of M n (from 2.40 kDa to 10.50 kDa) results in a two orders of magnitude increase in the carriers' mobility (from μsat = 4 × 10 -5 cm2 V-1 s-1 to μsat = 2 × 10-3 cm2 V-1 s-1). The obtained results underline the importance of the control of the macromolecular parameters in the preparation of electronic and electrochemical devices from poly(3,3″-dioctyl-2,2′5′,2″-terthiophene). The Royal Society of Chemistry 2006.
Medium band gap conjugated polymers from thienoacene derivatives and pentacyclic aromatic lactam as promising alternatives of poly(3-hexylthiophene) in photovoltaic application
Gao, Peili,Tong, Junfeng,Guo, Pengzhi,Li, Jianfeng,Wang, Ningning,Li, Cheng,Ma, Xuying,Zhang, Peng,Wang, Chenglong,Xia, Yangjun
, p. 85 - 95 (2018)
Two alternating medium band gap conjugated polymers (PBDT-TPTI and PDTBDT-TPTI) derived from 4,8-bis(4,5-dioctylthien-2-yl)benzo[1,2-b:4,5-b′]dithiophene (BDT-T) or 5,10-bis(4,5-didecylthien-2-yl)dithieno[2,3-d:2′,3′-d′]benzo[1,2-b:4,5-b′]dithiophene (DTBDT-T) with pentacyclic aromatic lactam of N,N-didodecylthieno[2′,3′:5,6]pyrido[3,4-g]thieno[3,2-c]-iso-quinoline-5,11-dione (TPTI), are synthesized and characterized. The comparative investigation of the photostabilities of the copolymers revealed that the PDTBDT-TPTI film exhibited the comparable photostability in relative to P3HT. Meanwhile, the inverted photovoltaic cells (i-PVCs) from the blend films of PBDT-TPTI and/or PDTBDT-TPTI with PC71BM, in which poly[(9,9-bis(3′-(N,N-dimethylamino)propyl)-2,7-fluorene)-alt-2,7-(9,9-dioctylfluorene)] were used as cathode modifying interlayer, presented higher power conversion efficiencies (PCEs) of 5.98% and 6.05% with photocurrent response ranging from 300 nm to 650 nm in contrast with the PCEs of 4.48% for the optimal inverted PVCs from P3HT/PC71BM under AM 1.5 G 100 mW/cm2. The PCEs of the i-PVCs from PBDT-TPTI and PDTBDT-TPTI were improved to 7.58% and 6.91% in contrast to that of 0.02% for the P3HT-based i-PVCs, and the photocurrent responses of the devices were extended to 300–792 nm, when the ITIC was used as electron acceptor materials. The results indicate that the PBDT-TPTI and PDTBDT-TPTI can be used as the promising alternatives of notable P3HT in the photovoltaic application.
Organic Thin-film Solar Cells Using Benzotrithiophene Derivatives Bearing Acceptor Units as Non-Fullerene Acceptors
Matsumoto, Kouichi,Yamashita, Kazuhiro,Sakoda, Yuuki,Ezoe, Hinata,Tanaka, Yuki,Okazaki, Tatsuya,Ohkita, Misaki,Tanaka, Senku,Aoki, Yuki,Kiriya, Daisuke,Kashimura, Shigenori,Maekawa, Masahiko,Kuroda-Sowa, Takayoshi,Okubo, Takashi
, p. 4620 - 4629 (2021/09/10)
New star-shaped non-fullerene acceptors (5Z,5′Z,5′′Z)-5,5′,5′′-((benzo[1,2-b : 3,4-b′ : 5,6-b′′]trithiophene-2,5,8-triyltris(4-octylthiophene-5,2-diyl))tris(methaneylylidene))tris(3-octyl-2-thioxothiazolidin-4-one) (1: BTT-OT-ORD) and 2,2′,2′′-((5Z,5′Z,5′′Z)-((benzo[1,2-b : 3,4-b′ : 5,6-b′′]trithiophene-2,5,8-triyltris(4-octylthiophene-5,2-diyl))tris(methaneylylidene))tris(3-octyl-4-oxothiazolidine-5,2-diylidene))trimalononitrile (2: BTT-OT-OTZDM) with a benzotrithiophene core, alkyl-thiophen units, and acceptor units were designed and synthesized. The HOMO-LUMO levels of 1 and 2 were determined by photoemission spectroscopy and UV-Vis absorption spectroscopy. Binary blend and ternary blend bulk heterojunction (BHJ) organic solar cells with non-fullerene acceptors 1 and 2 were fabricated with the inverted device structures of glass/ITO/ZnO/active_layer/MoO3/Ag. Both binary blend BHJ solar cells with 1 and 2 show lower JSC and larger VOC values than P3HT : PCBM solar cells. On the other hand, ternary blend BHJ organic solar cells, including 10 % of 1, exhibited a larger power conversion efficiency than P3HT : PCBM solar cells because the JSC value was largely improved.
Synthesis and characterization of new D-π-A and A-π-D-π-A type oligothiophene derivatives
Pandolfi, Fabiana,Rocco, Daniele,Mattiello, Leonardo
supporting information, p. 3018 - 3025 (2019/03/21)
In this work, we present a series of newly synthesized conjugated oligothiophene derivatives, with different numbers of central thiophene units, and different donor/acceptor architectures. Electrochemical and spectroscopic data have also been reported. We used thiophene or bithiophene as central donor core units, 3-octylthiophenes as π-bridge and solubilizing sub-units, and ethyl cyanoacetate or rhodanine moieties as acceptor end groups, in order to get D-π-A and A-π-D-π-A molecular architectures. The length of the synthesized oligothiophenes ranges from three to eight thiophene units, a variety that is sufficient to put in evidence different optical and electrochemical characteristics as well as semiconducting characteristics. Oligothiophene compounds can be regarded not only as models for the study of structure-property relationships relative to polythiophenes, but also they present a large number of applications in the field of organic electronics (i.e.: as donors in bulk-heterojunction solar cells and hole-transporting layer materials in perovskite solar cells, among others).
