Novel D(A-Ar)2 type small molecules with oligothiophene, diketopyrrolopyrrole and benzo[4,5]thieno [2,3-b]indole units: investigation on relationship between structure and property for organic solar cells

Published on Nov 24, 2016in Tetrahedron2.457
· DOI :10.1016/J.TET.2016.09.036
Hongrui Qi5
Estimated H-index: 5
(XTU: Xiangtan University),
Youming Zhang10
Estimated H-index: 10
(XTU: Xiangtan University)
+ 6 AuthorsWeiguo Zhu31
Estimated H-index: 31
(XTU: Xiangtan University)
Abstract Two novel D(A-Ar) 2 type small molecules (SMs) of 3T(DPP-BTI) 2 and 4T(DPP-BTI) 2 were synthesized and characterized, which contain diketopyrrolopyrrole (DPP) arms, 6-dodecyl-6 H -benzo[4,5]thieno[2,3- b ]indole (BTI) terminals, and oligomerthiophene donor unit (3T=trithiophene, 4T=tetrathiophene). The relation-ship between structure and property was investigated. Compared with their corresponding parent A-D-A type SMs, both D(A-Ar) 2 type SMs exhibited a significantly increasing circuit current density ( J sc ) by 1.39∼1.59 times and hole mobility (μ h ) by one order of magnitude, as well as a comparable power conversion efficiency (PCE) in their OPV and hole-only devices. The better photovoltaic properties with PCE of 3.02% and J sc of 10.41 mA cm −2 were obtained in the 3T(DPP-BTI) 2 based OPV cells. It indicates that appending the BTI terminal unit into A-D-A-type SMs is beneficial to increasing the J sc and μ h values of its resulting D(A-Ar) 2 type SMs in their corresponding devices.
📖 Papers frequently viewed together
9 Authors (Qiang Peng)
9 Authors (Jianhua Chen, ..., Weiguo Zhu)
#1K. Narayanaswamy (Indian Institute of Chemical Technology)H-Index: 9
#2A. Venkateswararao (Indian Institute of Chemical Technology)H-Index: 14
Last. Surya Prakash Singh (AcSIR: Academy of Scientific and Innovative Research)H-Index: 62
view all 5 authors...
A new low band gap small molecule DPP–DTF with a D–π–A–π–D molecular structure composed of a dithiafulvalene (DTF) donor and a diketopyrrolopyrrole (DPP) acceptor was synthesized and tested for organic solar cells. Using the DPP–DTF small molecule as an electron donor, and PC71BM as an acceptor a high power conversion efficiency (PCE) of 4.3% was achieved.
#1Deping Qian (Linköping University)H-Index: 24
#2Bo Liu (Linköping University)H-Index: 2
Last. Fengling Zhang (Linköping University)H-Index: 73
view all 14 authors...
In conjugated polymers and small molecules of organic solar cells, aggregation induced by intermolecular interactions governs the performance of photovoltaics. However, little attention has been paid to the connection between molecular structure and aggregation within solar cells based on soluble small molecules. Here we demonstrate modulation of intermolecular aggregation of two synthesized molecules through heteroatom substitution to develop an understanding of the role of aggregation in conju...
#1Bin KanH-Index: 37
#2Qian ZhangH-Index: 24
Last. Yongsheng ChenH-Index: 113
view all 11 authors...
Two acceptor–donor–acceptor small molecules based on thieno[3,2-b]thiophene-substituted benzo[1,2-b:4,5-b′]dithiophene, DRBDT-TT with alkyl side chain and DRBDT-STT with alkylthio side chain, were designed and synthesized. Both molecules exhibit good thermal stability, suitable energy levels, and ordered molecular packing. Replacing the alkyl chain with alkylthio increases the dihedral angle between the thieno[3,2-b]thiophene (TT) and benzo[1,2-b:4,5-b′]dithiophene (BDT) unit, and thus slightly ...
#1Jianqi ZhangH-Index: 55
#2Yajie ZhangH-Index: 25
Last. Zhixiang WeiH-Index: 41
view all 7 authors...
Ternary organic solar cells are promising candidates for bulk heterojunction solar cells; however, improving the power conversion efficiency (PCE) is quite challenging because the ternary system is complicated on phase separation behavior. In this study, a ternary organic solar cell (OSC) with two donors, including one polymer (PTB7-Th), one small molecule (p-DTS(FBTTH2)2), and one acceptor (PC71BM), is fabricated. We propose the two donors in the ternary blend forms an alloy. A notable averaged...
#1Jin-Liang WangH-Index: 23
#2Zhuo WuH-Index: 5
Last. Yong CaoH-Index: 127
view all 8 authors...
A family of narrow band gap extended π-conjugated D2-A2-D1-A1-D1-A2-D2 type small molecules based on diketopyrrolopyrrole derivatives as the stronger acceptor core (A1) coupled with indacenodithiophene (IDT; D1) and difluorobenzothiadiazole (A2) are synthesized, and their properties as donor materials in solution-processed small-molecule organic solar cells are investigated. The impacts of replacing the thiophene ring by a more electron-deficient thiazole ring and inserting thiophene spacer betw...
#1Ke Gao (SCUT: South China University of Technology)H-Index: 36
#2Lisheng Li (SCUT: South China University of Technology)H-Index: 11
Last. Xiaobin PengH-Index: 32
view all 12 authors...
We designed and synthesized the DPPEZnP-TEH molecule, with a porphyrin ring linked to two diketopyrrolopyrrole units by ethynylene bridges. The resulting material exhibits a very low energy band gap of 1.37 eV and a broad light absorption to 907 nm. An open-circuit voltage of 0.78 V was obtained in bulk heterojunction (BHJ) organic solar cells, showing a low energy loss of only 0.59 eV, which is the first report that small molecule solar cells show energy losses <0.6 eV. The optimized solar cell...
#1Hyosung Choi (UPR-RP: UPRRP College of Natural Sciences)H-Index: 28
#2Seo-Jin Ko (UNIST: Ulsan National Institute of Science and Technology)H-Index: 28
Last. Alan J. Heeger (UCSB: University of California, Santa Barbara)H-Index: 192
view all 9 authors...
: Small-bandgap polymer solar cells (PSCs) with a thick bulk heterojunction film of 340 nm exhibit high power conversion efficiencies of 9.40% resulting from high short-circuit current density (JSC ) of 20.07 mA cm(-2) and fill factor of 0.70. This remarkable efficiency is attributed to maximized light absorption by the thick active layer and minimized recombination by the optimized lateral and vertical morphology through the processing additive.
#1Qing-Ru Yin (BIT: Beijing Institute of Technology)H-Index: 2
#2Jingsheng Miao (SCUT: South China University of Technology)H-Index: 11
Last. Yong Cao (SCUT: South China University of Technology)H-Index: 127
view all 7 authors...
Two narrow-bandgap extended π-conjugated D2–Aw–D1–As–D1–Aw–D2 type small molecules (DPPBIT and DPPBIT4F) based on diketopyrrolopyrrole derivatives as the stronger acceptor core coupled with indacenodithiophene, benzothiadiazole or difluorobenzothiadiazole are designed and synthesized for application as donor materials in solution-processed small-molecule organic solar cells. The impacts of installation of four fluorine atoms to the two weaker acceptor units (benzothiadiazole) on the photophysica...
#1Bin Kan (NKU: Nankai University)H-Index: 37
#2Miaomiao Li (NKU: Nankai University)H-Index: 23
Last. Yongsheng Chen (NKU: Nankai University)H-Index: 113
view all 16 authors...
A series of acceptor–donor–acceptor simple oligomer-like small molecules based on oligothiophenes, namely, DRCN4T–DRCN9T, were designed and synthesized. Their optical, electrical, and thermal properties and photovoltaic performances were systematically investigated. Except for DRCN4T, excellent performances were obtained for DRCN5T–DRCN9T. The devices based on DRCN5T, DRCN7T, and DRCN9T with axisymmetric chemical structures exhibit much higher short-circuit current densities than those based on ...
#1Youming Zhang (XTU: Xiangtan University)H-Index: 10
#2Manjun Xiao (XTU: Xiangtan University)H-Index: 21
Last. Weiguo Zhu (XTU: Xiangtan University)H-Index: 31
view all 10 authors...
Three novel linear-shape small molecules of TPA(DPP-PN)(2), Cz(DPP-PN)(2) and Fl(DPP-PN)(2) were synthesized and characterized, which contain the same arm of diketopyrrolopyrrole (DPP) and large aryl terminals of phenanthrene (PN), as well as different aryl centers of triphenylamine( TPA), carbazole (Cz) and fluorene (Fl), respectively. Narrower optical band gaps (1.62-1.69 eV) and lower highest occupied molecular orbital energy levels (-5.71 to -5.79 eV) were observed in these small molecules c...
Cited By5
#1Tsubasa Matsuzawa (Tokyo Medical and Dental University)H-Index: 6
#2Takamitsu Hosoya (Tokyo Medical and Dental University)H-Index: 44
Last. Suguru Yoshida (Tokyo Medical and Dental University)H-Index: 30
view all 3 authors...
An aryne reaction with alkynyl sulfides affording benzo[b]thiophenes is disclosed. A wide range of 3-substituted benzothiophenes were synthesized from easily available o-silylaryl triflates and alkynyl sulfides in a one-step intermolecular manner. The synthesis of diverse multisubstituted benzothiophene derivatives involving a pentacyclic compound was achieved by virtue of the good functional group tolerance and versatile C2 functionalizations.
#2Phuong Hoang Tran (VNUHCM: Vietnam National University, Ho Chi Minh City)H-Index: 16
In this study, we have developed the synthesis of thieno[2,3-b]indole dyes via a multicomponent reaction of cheap and available reagents such as sulfur, acetophenones, and indoles using a magnetic nanoparticle-supported [Urea]4[ZnCl2] deep eutectic solvent as a green catalyst. The synthesis of a series of diversely functionalized thieno[2,3-b]indole has been successfully performed in a one-pot reaction. Among a total of 25 compounds synthesized, there are 21 new compounds with full characterizat...
#1I. M. Sakhautdinov (RAS: Russian Academy of Sciences)H-Index: 5
#2R. N. Malikova (RAS: Russian Academy of Sciences)H-Index: 3
Last. M. S. Yunusov (RAS: Russian Academy of Sciences)H-Index: 13
view all 8 authors...
New cyclopentene-fused [C60]-fullerene derivatives containing terpene moieties have been synthesized by [3 + 2]-addition to fullerene C60. All obtained products were fully characterized by 1H- and 13C-NMR, IR, and MS. The electrochemical properties have been studied by cyclic voltammograms (CV), combined with absorption spectra, which are consistent with those obtained from density functional theory (DFT) calculations. It was found that all fulleropyrrolidines showed very similar absorption spec...
#1Muhammad Naeem Shah (ZJU: Zhejiang University)H-Index: 5
#2Shuhua Zhang (ZJU: Zhejiang University)H-Index: 12
Last. Chang-Zhi Li (ZJU: Zhejiang University)H-Index: 59
view all 6 authors...
Abstract The alternating diketopyrrolopyrrole (DPP)-Quinoxaline (Qx) based conjugated polymers are synthesized and investigated as electron donors for polymer solar cells (PSCs). Through the substitution of phenyl in Qx unit at para ( p ) and meta ( m ) positions with methoxy group, the resultant DPP- p MQx and DPP- m MQx polymers possess narrow optical band gap (1.32 and 1.26 eV) with relatively low-lying highest occupied molecular orbitals. The obtained photovoltaic devices indicate that the c...
#8Qiang Peng (Sichuan University)H-Index: 29
Abstract A novel type of the benzo[4,5]thieno[2,3- b ]indole (BTI)-terminated small molecules (SMs) with a D′(A-D) 2 framework were synthesized and characterized, i.e. BDT(DPP- 9 -BTI) 2 , BDT(DPP- 8 -BTI) 2 and 2T(DPP- 8 -BTI) 2 , in which the central donor (D′) units are benzodithiene (BDT) and dithiophene (2T), the armed acceptor (A) unit is dithienyl-diketopyrrolopyrrole (DPP), and the terminated donor (D) unit is BTI with different substituted position. For comparison, the SMs with a D-A-D ...
This website uses cookies.
We use cookies to improve your online experience. By continuing to use our website we assume you agree to the placement of these cookies.
To learn more, you can find in our Privacy Policy.