1160823-78-8

Basic information

• Product Name: 1,1'-[4,8-Bis[(2-ethylhexyl)oxy]benzo[1,2-b:4,5-b']dithiophene-2,6-diyl]bis[1,1,1-trimethylstannane]
• Synonyms: 1,1'-[4,8-Bis[(2-ethylhexyl)oxy]benzo[1,2-b:4,5-b']dithiophene-2,6-diyl]bis[1,1,1-trimethylstannane];2,6-Bis(trimethyltin)-4,8-bis(2-ethylhexyloxy)benzo[1,2-b:4,5-b'] dithiophene;2Sn-BDT-OEH;2,6‐bis(triMethyltin)‐ 4,8‐ bis‐(2‐ethylhexyloxy) benzo[1,2‐ b;2,6-Bis(2MeSn)-4,8-bis(2-OEH)benzo[1,2-b:4,5-b']dithiophene;Stannane, 1,1'-[4,8-bis[(2-ethylhexyl)oxy]benzo[1,2-b:4,5-b']dithiophene-2,6-diyl]bis[1,1,1-triMethyl- 2,6-Bis(triMethyltin)-4,8-bis(2-ethylhexyloxy)benzo[1,2-b:4,5-b']dithiophene;(4,8-Bis((2-ethylhexyl)oxy)benzo[1,2-b:4,5-b']dithiophene-2,6-diyl)bis(triMethylstannane);Stannane, 1,1'-[4,8-bis[(2-ethylhexyl)oxy]benzo[1,2-b:4,5-b']dithiophene-2,6-diyl]bis[1,1,1-triMethyl-
• CAS NO: 1160823-78-8
• Molecular Formula: C₃₂H₅₄O₂S₂Sn₂
• Molecular Weight: 772.29
• Mol File: 1160823-78-8.mol
• Article Data: 28

Chemical Properties

• Melting Point: 70-75°C
• Boiling Point: 665.1±65.0 °C(Predicted)
• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 1,1'-[4,8-Bis[(2-ethylhexyl)oxy]benzo[1,2-b:4,5-b']dithiophene-2,6-diyl]bis[1,1,1-trimethylstannane](CAS DataBase Reference)
• NIST Chemistry Reference: 1,1'-[4,8-Bis[(2-ethylhexyl)oxy]benzo[1,2-b:4,5-b']dithiophene-2,6-diyl]bis[1,1,1-trimethylstannane](1160823-78-8)
• EPA Substance Registry System: 1,1'-[4,8-Bis[(2-ethylhexyl)oxy]benzo[1,2-b:4,5-b']dithiophene-2,6-diyl]bis[1,1,1-trimethylstannane](1160823-78-8)

Safety Data

• Hazard Codes: T
• Statements: 23/24/25
• Safety Statements: 45
• RIDADR: UN 3146 6.1 / PGIII
• WGK Germany: 3
• Hazardous Substances Data: 1160823-78-8(Hazardous Substances Data)

Usage

Application

Benzo[1,2-b:4,5-b'']dithiophene (BDT) is one of the widely used building blocks to produce polymer structures for highly efficient organic solar cells, in a blend with fullerene or non-fullerene acceptors.

Uses

Different sources of media describe the Uses of 1160823-78-8 differently. You can refer to the following data:
1. Used as an electron donor in Polymer Solar Cells (PSC).
2. Synthesis of polymers for high power conversion efficiency (PCE) organic solar cells and OFETs
3. suzuki reaction

Upstream product

• 32281-36-0 4,8-dihydrobenzo[1,2-b:4,5-b']dithiophene-4,8-dione 
• 1653-16-3 3-(iodomethyl)heptane 
• 1160823-77-7 4,8-di(2-ethylhexyloxy)benzo[1,2-b:4,5-b']dithiophene 
• 18908-66-2 3-bromomethylheptane 
• 1226782-13-3 2,6-dibromo-4,8-bis((2-ethylhexyl)oxy)-benzo[1,2-b:4,5-b′]dithiophene 
• 1066-45-1 trimethyltin(IV)chloride 
• 104-76-7 2-Ethylhexyl alcohol 
• 1357156-35-4 4,8-dihydroxybenzo[1,2-b:4,5-b']dithiophene 
• 78016-72-5 2-ethylhexyl 4-methylbenzenesulfonate 

Relevant articles and documents

A facile strategy to enhance the fill factor of ternary blend solar cells by increasing charge carrier mobility

Two conjugated polymers based on benzo[1,2-b:4,5-b′]dithiophene (BDT) with triethylene glycol (TEG) and ethylhexyl side chains (abbreviated as PBDTT-TEG and PBDTT-EH, respectively) were designed and synthesized. A polymer field-effect transistor of PBDTT-TEG exhibited a charge carrier mobility nearly one order of magnitude higher than that of PBDTT-EH. Measurements on polymer solar cells (PSCs) based on polymer:[6,6]-phenyl-C71-butyric acid methyl ester (PC71BM) binary blends showed the PBDTT-TEG-based devices had higher short-circuit current density (Jsc) than PBDTT-EH. The effect of the incorporation of PBDTT-TEG into PBDTT-EH on the photovoltaic properties has been investigated by blending them together with different ratios. The optimization of the devices showed an obvious increase in fill factor (FF) values and an improvement in efficiency compared with their binary ones, which is ascribed to a higher charge mobility and higher crystallinity of PBDTT-TEG.

Comparison of thiophene- and selenophene-bridged donor-acceptor low band-gap copolymers used in bulk-heterojunction organic photovoltaics

We report a detailed comparison of absorption spectroscopy, electrochemistry, DFT calculations, field-effect charge mobility, as well as organic photovoltaic characteristics between thiophene- and selenophene-bridged donor-acceptor low-band-gap copolymers. In these copolymers, a significant reduction of the band-gap energy was observed for selenophene-bridged copolymers by UV-visible absorption spectroscopy and cyclic voltammetry. Field-effect charge mobility studies reveal that the enhanced hole mobility of the selenophene-bridged copolymers hinges on the solubilising alkyl side chain of the copolymers. Both cyclic voltammetry experiments and theoretical calculations showed that the decreased band-gap energy is mainly due to the lowering of the LUMO energy level, and the raising of the HOMO energy level is just a secondary cause. These results are reflected in a significant increase of the short circuit current density (JSC) but a slight decrease of the open circuit voltage (VOC) of their bulk-heterojunction organic photovoltaics (BHJ OPVs), of which the electron donor materials are a selenophene-bridged donor-acceptor copolymer: poly{9-dodecyl-9H-carbazole-alt-5, 6-bis(dodecyloxy)-4,7-di(selenophen-2-yl) benzo[c][1,2,5]-thiadiazole} (pCzSe) or poly{4,8-bis(2-ethylhexyloxy)benzo[1,2-b;4,5-b′]dithiophene-alt-5,6- bis(dodecyloxy)-4,7-di(selenophen-2-yl)benzo[c][1,2,5]-thiadiazole} (pBDTSe), or a thiophene-bridged donor-acceptor copolymer: poly{9-dodecyl-9H-carbazole-alt- 5,6-bis(dodecyloxy)-4,7-di(thiophen-2-yl)benzo[c][1,2,5]-thiadiazole} (pCzS) or poly{4,8-bis(2-ethylhexyloxy)benzo[1,2-b;4,5-b′]dithiophene-alt-5, 6-bis(dodecyloxy)-4,7-di(thiophen-2-yl)benzo[c][1,2,5]-thiadiazole} (pBDTS); the electron acceptor material is [6,6]-phenyl-C61-butyric acid methyl ester (PCBM). Judging from our device data, the potential Se-Se interactions of the selenophene-bridged donor-acceptor copolymers, which is presumably beneficial for the fill factor (FF) of BHJ OPVs, is rather susceptible to the device fabrication conditions.

Organic Semiconductor Compound, Organic Thin Film Including the Organic Semiconductor Compound and Electronic Device Including the Organic Thin Film

Provided is an organic semiconductor compound which is represented by chemical formula 1 or 2. Moreover, provided is an organic thin film containing the same. In the chemical formulas 1 and 2, each substituent is the same as defined in the present specification. According to the present invention, it is possible to reduce production costs for devices.COPYRIGHT KIPO 2018

Dithieno[3,2-b:2′,3′-d]pyrrole-benzo[c][1,2,5]thiadiazole conjugate small molecule donors: Effect of fluorine content on their photovoltaic properties

Two new small molecule donors, namely ICT4 and ICT6 with D1-A-D2-A-D1 architecture having 2,4-bis(2-ethylhexyl)-4H-dithieno[3,2-b:2′,3′-d]pyrrole (EHDTP, D1) and 4,8-bis((2-ethylhexyl)oxy)benzo[1,2-b:4,5-b′]dithiophene (OBDT, D2) as the terminal and central donor, and benzo[c][1,2,5]thiadiazole (BT for ICT4) and 5,6-difluorobenzo[c][1,2,5]thiadiazole (F2BT for ICT6) as the acceptor (A) moieties, are synthesized and their optical, electronic and photovoltaic properties are investigated. Both ICT4 and ICT6 have considerable solubility in various solvents and possess efficient light absorption ability [ε (×105 mol-1 cm-1) is 0.99 and 1.06, respectively for ICT4 and ICT6] and appropriate frontier molecular orbital energy offsets with [6,6]-phenyl-C71-butyric acid methyl ester (PC71BM). Bulk heterojunction solar cells (BHJSCs) are fabricated using ICT4/ICT6 and PC71BM as donors and acceptors, respectively and BHJSCs with two-step annealed (thermal followed by solvent vapor annealing) active layers of ICT4 and ICT6 show overall power conversion efficiencies (PCEs) of 5.46% and 7.91%, respectively. The superior photovoltaic performance of the ICT6 based BHJSCs is due to the favourable morphology with a nanoscale interpenetrating network in the ICT6:PC71BM active layer induced by the fluorine atoms on the BT acceptor, which significantly enhances the dissociation of excitons, charge transport and the charge collection efficiency, and suppresses bimolecular recombination in the BHJ. The observed higher PCE of 7.91% indicates that ICT6 is one of the best BT based donor material for small molecular BHJSCs.

Dithienopyrrole-benzodithiophene based donor materials for small molecular BHJSCs: Impact of side chain and annealing treatment on their photovoltaic properties

Two small molecular organic materials denoted as ICT1 and ICT2 with A-D1-D2-D1-A architecture have been synthesized and their thermal, photo-physical, electrochemical and photovoltaic properties are explored. Synthesized materials have n-butylrhodanine acceptor (A), dithienopyrrole (DTP) (D1) and benzodithiophene (BDT) (D2) (Alkoxy BDT and alkylthiophene BDT, respectively for ICT1 and ICT2) donor moieties. Both the materials have good solubility (up to 25 mg/mL) in most common organic solvents and have excellent thermal stability with the decomposition temperature (Td) as 348 and 382 °C, respectively for ICT1 and ICT2. Both ICT1 and ICT2 have broad and intense visible region absorption (molar excitation coefficient is 1.71 × 105 and 1.65 × 105 mol?1 cm?1, respectively for ICT1 and ICT2) and have suitable HOMO and LUMO energy levels for PC71BM acceptor. Bulk heterojunction solar cells with ITO/PEDOT:PSS/blend/Al structure are fabricated using these materials. The BHJSCs fabricated by spin cast of ICT1:PC71BM and ICT2:PC71BM (1:2 wt ratio) blend from chloroform showed power conversion efficiency (PCE) of 2.77% (Jsc = 6.84 mA/cm2, Voc = 0.92 V and FF = 0.44) and 3.27% (Jsc = 7.26 mA/cm2, Voc = 0.96 V and FF = 0.47), respectively. Annealing the active layer significantly improved the PCE of these BHJSCs to 5.12% (Jsc = 10.15 mA/cm2, Voc = 0.87 V and FF = 0.58) and 5.90% (Jsc = 10.68 mA/cm2, Voc = 0.92 V and FF = 0.60), respectively for ICT1 and ICT2 donors. The enhancement in the PCE is due to higher light harvesting ability of the active layer, better nanoscale morphology for efficient and balanced charge transport and effective exciton dissociation at the donor-acceptor interface.