143367-56-0

Basic information

• Product Name: 5,5'‐ bis(triMethylstannyl)‐ 2,2'‐bithiophene
• Synonyms: 5,5'‐ bis(triMethylstannyl)‐ 2,2'‐bithiophene;5,5'-Bis(trimethyltin)-2,2'-bithiophene;5,5-Ditrimethylstannyl-2,2'-bithiophene;5,5'-Bis(trimethylstannyl)-2,2'-bithiophene 97%;Chemical Name:;5,5'-Bis-trimethylstannanyl-[2,2']bithiophenyl
• CAS NO: 143367-56-0
• Molecular Formula: C₁₄H₂₂S₂Sn₂
• Molecular Weight: 492.88242
• Product Categories: Thiophene
• Mol File: 143367-56-0.mol
• Article Data: 20

Chemical Properties

• Melting Point: 96-100°C
• Boiling Point: 418.2±55.0 °C(Predicted)
• Appearance: /
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• CAS DataBase Reference: 5,5'‐ bis(triMethylstannyl)‐ 2,2'‐bithiophene(CAS DataBase Reference)
• NIST Chemistry Reference: 5,5'‐ bis(triMethylstannyl)‐ 2,2'‐bithiophene(143367-56-0)
• EPA Substance Registry System: 5,5'‐ bis(triMethylstannyl)‐ 2,2'‐bithiophene(143367-56-0)

Safety Data

• Hazard Codes: T+,N
• Statements: 26/27/28-50/53
• Safety Statements: 26-27-28-45-60-61
• RIDADR: UN 3146 6.1 / PGIII
• WGK Germany: 3
• Hazardous Substances Data: 143367-56-0(Hazardous Substances Data)

Usage

Description

5,5'-bis(trimethylstannyl)-2,2'-bithiophene?can be used for the synthesis of small molecules and polymer semiconductors for OFETs, OLED, PLED, OPV applications.5,5'-bis(trimethylstannyl)-2,2'-bithiophene can be prepared from 2,2'-bithiophene which is an electron rich and donating unit if it is embedded into low band-gap polymer semiconductors.

Upstream product

• 492-97-7 2,2'-Bithiophene 
• 1066-45-1 trimethyltin(IV)chloride 
• 4805-22-5 5,5'-dibromo-2,2'-bisthiophene 
• 17946-71-3 (trimethylstannyl)lithium 

Downstream Products

• 923001-29-0 5,5'-bis-[bis-(4-tert-butyl-phenyl)-boranyl]-[2,2']bithiophenyl 
• 1451736-96-1 C₅₀H₃₄N₄S₄ 
• 561068-09-5 5,5'''-dibromo-3,3'''-bis(dodecyl)-2,2':5',2'':5'',2'''-quarterthiophene 
• 162151-09-9 3,3?-didodecyl-2,2′;5′,2″;5″,2?-quaterthiophene 
• 1174670-67-7 C₂₈H₂₀N₂S₂ 

Relevant articles and documents

Side-Chain-Induced Rigid Backbone Organization of Polymer Semiconductors through Semifluoroalkyl Side Chains

While high-mobility p-type conjugated polymers have been widely reported, high-mobility n-type conjugated polymers are still rare. In the present work, we designed semifluorinated alkyl side chains and introduced them into naphthalene diimide-based polymers (PNDIF-T2 and PNDIF-TVT). We found that the strong self-organization of these side chains induced a high degree of order in the attached polymer backbones by forming a superstructure composed of "backbone crystals" and "side-chain crystals". This phenomenon was shown to greatly enhance the ordering along the backbone direction, and the resulting polymers thus exhibited unipolar n-channel transport in field-effect transistors with remarkably high electron mobility values of up to 6.50 cm2 V-1 s-1 and with a high on-off current ratio of 105.

Direct arylation polymerization toward a narrow bandgap donor–acceptor conjugated polymer of alternating 5,6-difluoro-2,1,3-benzothiadiazole and alkyl-quarternarythiophene: From synthesis, optoelectronic properties to devices

ABSTRACT: Direct arylation polymerization (DAP) enabled facile synthesis of a narrow bandgap donor–acceptor conjugated polymer (PDFBT-Th4) composed of alternating 5,6-difluoro-2,1,3-benzothiadiazole and alkyl-quaternarythiophene. The optimized reaction condition of DAP catalyzed with Pd(OAc)2/(o-MeOPh)3P/PivOH/K2CO3 in o-xylene led to the target polymer with a number-average molecular weight (Mn) of 14.6 kDa without noticeable homocoupling or β-branching defects. UV-vis absorption spectra of PDFBT-Th4 indicate strong interchain aggregation in films. While the C-H selectivity and the alternating polymer structure of PDFBT-Th4 synthesized via DAP are comparable to those of the same type polymers synthesized via Stille coupling, the batch of PDFBT-Th4 synthesized via optimal DAP, despite its lower Mn, showed higher hole mobility in field effect transistors and larger power conversion efficiency in organic solar cell devices. These results further demonstrate the promising potential of DAP for efficient synthesis of high-performance D-A conjugated polymers for broad optoelectronic applications.

Ortho-bridged perylene diimide dimer and preparation method thereof as well as application thereof in organic photovoltaic devices

The invention provides an ortho-bridged perylene diimide dimer (formula I), a preparation method and an application thereof in the organic photovoltaic field. The invention further relates to an organic solar cell of the compound and a preparation method of the organic solar cell. Compared with a PDI monomer molecule, a formed twisted dimer structure is capable of effectively weakening excessive aggregation among PDI molecules, so that the phase size is reduced. Meanwhile, by virtue of ortho-bridging, the deformation of a PDI inner core caused by waist bridging can be avoided, so that certain planarity and relatively strong pi-pi accumulation can be maintained, and relatively high electronic mobility can be obtained. The PDI dimer is taken as a receptor material and is combined with an electron donor polymer so as to prepare the organic solar cell, so that very high photoelectric conversion efficiency is realized.

A molecular structure and crystallization correlation study of pyromellitic diimide-based conjugated copolymers

Three pyromellitic diimide(PMDI)-based polymers—poly(pyromellitic diimide-co-bithiophene) [poly(PMDI-BTh)], poly(pyromellitic diimide-co-tetrathiophene) [poly(PMDI-TTh)], and poly(pyromellitic diimide-co-benzodithio- phene) [poly(PMDI-BDTTh)]—are synthesized to study the influence of different thiophene-containing electron-donating groups on the crystallizability of PMDI-based conjugated polymers. Computer simulation using Density Functional Theory (DFT) [Gaussian B3LYP/6–31 + G(d,p)] indicates that poly(PMDI-BDTTh) has a more planar molecular structure than the other two copolymers. Powder XRD diffraction experiment of the poly(PMDI-BDTTh) shows a diffraction peak at about 2θ = 6.0°, but no diffraction peak occurs for poly(PMDI-BTh) and poly(PMDI-TTh). Although PMDI is a planar structure that is favorable for the molecular aggregation, a comonomer with planar structure seems to be very crucial in order to synthesize a crystallizable push–pull-type PMDI-based conjugated copolymer.