1352642-37-5

Basic information

• Product Name: 2,6-Bis(triMethyltin)-4,8-bis(5-(2-ethylhexyl)thiophen-2-yl)benzo [1,2-b:4,5-b']dithiophene
• Synonyms: 1,1'-[4,8-Bis[5-(2-ethylhexyl)-2-thienyl]benzo[1,2-b:4,5-b']dithiophene-2,6-diyl]bis[1,1,1-trimethylstannane];Stannane, 1,1'-[4,8-bis[5-(2-ethylhexyl)-2-thienyl]benzo[1,2-b:4,5-b']dithiophene-2,6-diyl]bis[1,1,1-triMethyl-;4,8-Bis[5-(2-ethylhexyl)thiophen-2-yl]-2,6-bis(trimethylstannyl)benzo[1,2-b:4,5-b']dithiophene;2,6-bis(trimethylstannyl)-4,8-bis(5-(2-ethylhexyl)thiophen-2-yl)benzo[1,2-b:4,5-b']dithiophene;4,8-Bis[5-(2-ethylhexyl)thiophen-2-yl]-2,6-bis(trimethylstannyl)benzo[1,2-b:4,5-b']dithiophene;2,6-Bis(triMethyltin)-4,8-bis(5-(2-ethylhexyl)thiophen-2-yl)benzo [1,2-b:4,5-b']dithiophene;(4,8-bis(5-(2-ethylhexyl)thiophen-2-yl)benzo[1,2-b:4,5-b']dithiophene-2,6-diyl)bis(triMethylstannane);2,6-Bis(triMethyltin)-4,8-bis(5-(2-ethylhexyl)thiophen-2-yl)benzo [1,2-b:4,5-
• CAS NO: 1352642-37-5
• Molecular Formula: C₄₀H₅₈S₄Sn₂
• Molecular Weight: 904.56852
• EINECS: -0
• Mol File: 1352642-37-5.mol
• Article Data: 19

Chemical Properties

• Boiling Point: 767.8±70.0 °C(Predicted)
• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 2,6-Bis(triMethyltin)-4,8-bis(5-(2-ethylhexyl)thiophen-2-yl)benzo [1,2-b:4,5-b']dithiophene(CAS DataBase Reference)
• NIST Chemistry Reference: 2,6-Bis(triMethyltin)-4,8-bis(5-(2-ethylhexyl)thiophen-2-yl)benzo [1,2-b:4,5-b']dithiophene(1352642-37-5)
• EPA Substance Registry System: 2,6-Bis(triMethyltin)-4,8-bis(5-(2-ethylhexyl)thiophen-2-yl)benzo [1,2-b:4,5-b']dithiophene(1352642-37-5)

Safety Data

• RIDADR: UN 3146 6.1/PG I
• HazardClass: 6.1
• PackingGroup: I
• Hazardous Substances Data: 1352642-37-5(Hazardous Substances Data)

Usage

Description

2,6-Bis(trimethytin)-4,8-bis(5-(2-ethylhexyl)thiophen-2-yl)benzo[1,2-b:4,5-b’]dithiophene?has been used for the synthesis of small molecules and low band gap polymer semiconductors such as PTB-7, PCE10 (also called PTB7-Th or PBDTTT-EFT) and PBDB-T (PCE12) for OFETs, OLED, PLED, OPV applications.

Upstream product

• 4891-44-5 2-(2-ethylhexyl)thiophen 
• 32281-36-0 4,8-dihydrobenzo[1,2-b:4,5-b']dithiophene-4,8-dione 
• 18908-66-2 3-bromomethylheptane 
• 1352642-35-3 4-(5-(2-ethylhexyl)thiophen-2-yl)-8-(5-(2-ethylhexyl)thiophene-2-yl)benzo[1,2-b:4,5-b']dithiophene 
• 1066-45-1 trimethyltin(IV)chloride 

Relevant articles and documents

Structure evolution from D-A-D type small molecule toward D-A-D-A-D type oligomer for high-efficiency photovoltaic donor materials

In order to study the influence of structure evolution on properties, a D-A-D-A-D-type oligomer of 5BDTBDD and its D-A-D type small molecule of 3BDTBDD were designed and synthesized, which consist of electron-accepting (A) unit of benzo [1,2-c:4,5-c'] dithiophene-4,8-dione (BDD) and electron-donating (D) unit of 4,8-di (6-ethylhexylthiophen-2-yl)benzo [1,2-b:4,5-b']dithiophene (BDT). The effect of structure evolution on crystallinity, absorption, mobility, morphology and photovoltaic properties was primarily investigated. It is found that, by simply inserting a D-A repeat unit, 5BDTBDD shows more improved crystallization, absorption, mobility and morphology than 3BDTBDD. As a result, 5BDTBDD exhibits better photovoltaic properties than 3BDTBDD in their non-fullerene organic solar cells using 9-bis(2-methylene-(3-(1,1-dicyanomethylene)-indanone))-5,5,11,11-tetrakis (4-hexylphenyl)-di thieno [2,3-d:2′,3′-d']-s-indaceno [1,2-b:5,6-b'] dithiophene (ITIC) as acceptor material. An increasing power conversion efficiency of 7.89% is obtained in the 5BDTBDD:ITIC cells, which is 1.8 times higher than that value (4.33%) in the 3BDTBDD:ITIC cells. It indicates that structure evolution from D-A-D type small molecule toward D-A-D-A-D type oligomer is an efficient strategy to achieve high-efficiency donor materials in organic solar cells.

Enhanced and controllable open-circuit voltage using 2D-conjugated benzodithiophene (BDT) homopolymers by alkylthio substitution

In this study, we explore the effects of alkylthiophene (T) and alkylthiothiophene (T-S) substituents on the benzo[1,2-b;4,5-b′]dithiophene (BDT) unit by comparing the BDTT homopolymer (PBDTT), the BDTT-alt-BDTT-S copolymer (PBDTT-BDTT-S), and the BDTT-S homopolymer (PBDTT-S) in terms of UV-visible absorption spectra, cyclic voltammetry (CV) results, computational calculations, and experimental results. The T-S substituent increased the hole mobility of the polymer and down-shifted the highest occupied molecular orbital (HOMO) energy level of the polymer, leading to slight red-shifting of the absorption spectrum. The organic photovoltaic (OPV) cells based on PBDTT-S as a donor and [6,6]-phenyl-C71-butylic acid methyl ester (PC71BM) as an acceptor demonstrated a high power conversion efficiency (PCE) of 7.05% under AM 1.5G illumination (100 mW cm-2). To the best of our knowledge, this PCE value is one of the highest values reported for homopolymer donor-based OPVs. Compared to the well-known P3HT homopolymer, which shows a similar absorption profile, PBDTT-S is a promising candidate for organic photodiodes.

Synthesis and application of (D-A)n+1D type oligomer photovoltaic donor material based on benzodithiophene-4,8-dione

The invention relates to a benzo[1,2-c,4,5-c']dithiophene-4,8-dione (BDD)-based electron acceptor, synthesis of an oligomer photovoltaic donor material with a (D-A)n+1D (n is equal to 1,2. . .) framework as well as application of the oligomer photovoltaic donor material to an organic solar battery. The oligomer comprises thiophene, benzene, benzodithiophene and a derivative electron donating (D) unit as well as BDD and a derivative electron acceptor (A) unit, and can serve as a donor material widely applied to a solution processing type organic solar battery. When a light active layer donor material is 5 BDTBDD, an acceptor material is 3,9-bis(2-methylene-3-(1,1-dicyanomethyl)indolone)-5,5,11,11-tetra(4-hexylphenyl)- dithiolato[2,3d,2',3'd]-s-indole[1,2-b,5,6']dithiophene (ITIC), and the highest energy conversion efficiency of bulk heterojunction oligomer solar energy is 7.89 percent when the mass ratio of the donor to the acceptor is 1,0.8. The organic solar battery is constructed bytaking the oligomer as the electron donor material and non-fullerene as the electron acceptor material, and efficient energy conversion of the device is realized.

Synthesis and correlation between structure and photovoltaic performance of two-dimensional BDT-TPD polymers

Four BDT-TPD polymers (PA-PD) were synthesized by modifying the alkylthienyl chains on BDT, placing spacer group between BDT and TPD, and installing extended conjugated side chains on the BDT of the polymer to investigate the correlation between structure and photovoltaic performance for these polymers. The molecular weight of PA-PD polymers ranged from the highest (Mn = 80 kDa for PA) to the lowest (Mn = 7.9 kDa for PD), and their decomposition temperatures at 5% weight loss were in the range 401-435 °C. PA, PB, and PC showed similar UV-vis absorption spectra; however, PD showed much broader absorption spectrum in the entire UV-vis region, because of the extended conjugated side chains. The HOMO levels of the polymers were -5.72, -5.63, -5.48, and -5.61 eV for PA, PB, PC, and PD, respectively, indicating very low-lying HOMO energy levels. The bandgaps of these polymers were calculated and found to be in the range 1.85-1.88 eV. The theoretical calculations clearly show that the torsional angles between the alkylthienyl group and BDT unit of the simplified dimer correlated to the π-orbital delocalization, suggesting that the HOMO π-electrons of vertically aligned conjugated side chains do not delocalize well in the polymers such as PA, PB, and PC bearing high torsional angles. The optimized weight ratios of the polymer to PC61BM were determined to be 1:1, 1:1.5, and 1:1 for PA, PC, and PD, respectively, and the average PCEs of the devices were 5.36%, 4.62%, and 2.74% for PA, PC, and PD, respectively, after optimization with 1,8-diiodooctane (DIO). A relatively small amount of DIO as an additive was necessary to reach the optimal PCEs of the devices, and the device incorporating PC needed only 0.5% DIO to obtain the best PCE. The AFM study reveals that the blend films after adding DIO showed much smooth morphologies, and the blend film of PA exhibited more crystalline property, as shown by the XRD analysis.