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Usage

Uses

Used in Pharmaceutical Industry:
(4,4'-didodecyl-2,2'-bithiophene-5,5'-diyl)bis(trimethylstannane) is used as a building block for the development of complex compounds, particularly in the synthesis of polymers. Its unique structure, which includes sulfur atoms and long carbon chains, may contribute to the creation of novel pharmaceutical compounds with potential therapeutic applications.
Used in Chemical Engineering:
In the chemical engineering field, (4,4'-didodecyl-2,2'-bithiophene-5,5'-diyl)bis(trimethylstannane) serves as a precursor or intermediate in the synthesis of other complex compounds. Its organometallic nature and structural features may be exploited to produce new materials with specific properties, such as improved stability or reactivity, for various chemical processes and applications.

Upstream product

• 345633-76-3 4,4’-bis(dodecyl)-2,2’-bithiophene 
• 1066-45-1 trimethyltin(IV)chloride 
• 104934-52-3 3-dodecylthiophene 
• 15890-72-9 laurylmagnesium bromide 

Relevant academic research and scientific papers

High charge carrier mobility, low band gap donor-acceptor benzothiadiazole-oligothiophene based polymeric semiconductors

A series of benzothiadiazole oligothiophene and oligo(thienylene vinylene) donor-acceptor (D-A) copolymers were synthesized and characterized. These low optical band gap materials (～1.5 eV) are capable of absorbing photons in the range of 400-800 nm and exhibit good thermal stability. Their hole mobilities, determined using an organic field-effect transistor (OFET) architecture, vary over a range of 3 orders of magnitude and strongly correlate with the molecular ordering and morphology of the respective thin films. Spin-coated films of the poly(benzothiadiazole-sexithiophene) PBT6, which exhibits a highly crystalline lamellar π-π stacked edge-on orientation on the OFET substrate, possesses a hole mobility of ca. 0.2 cm2/V·s. Vinylene-containing analogs PBT6V2 and PBT6V2′ are amorphous and exhibit very low mobilities. The molecular weight of PBT6 has a strong influence on the electronic properties: a sample with a lower molecular weight exhibits a mobility approximately 1 order of magnitude lower than the high molecular weight homologue, and the absorption maximum is appreciably blue-shifted. The hole mobility of PBT6 is further enhanced by a factor of ca. 3 through fabrication of the OFET by drop casting. OFETs fabricated by this process exhibit mobilities of up to 0.75 cm2/V·s and ION/OFF ratios in the range of 106-107. These results demonstrate the potential of incorporating benzothiadiazole units into polythiophene derivatives to develop high-mobility semiconducting polymers.

Synthesis and characterization of a novel ambipolar polymer semiconductor based on a fumaronitrile core as an electron-withdrawing group

Two conjugated polymers containing stilbene and fumaronitrile moieties were synthesized to investigate their electronic properties by the existence of electron-withdrawing cyano groups on a vinylene backbone. The cyclic voltammetry investigation and time-dependent density functional theory calculations indicated that the cyano substituents lowered the lowest unoccupied molecular orbital (LUMO) energy level by about 0.65 and 0.63 eV, respectively. The lowering of the LUMO energy levels due to the electron-withdrawing properties of the cyano substituents could enhance electron injection capability. Furthermore, bithiophene-fumaronitrile (donor-acceptor) intermolecular interaction facilitates the self-assembly of the polymer chains. Organic field-effect transistors (OFETs) based on PBTSB without the electron-withdrawing group only exhibit hole transport, while OFETs based on PBTFN with cyano substituents exhibit ambipolar characteristics. The growth of PBTFN crystalline fibrils was observed with increasing annealing temperature, which enhanced hole and electron mobility. A complementary-like inverter using PBTFN with ambipolar properties exhibited good symmetry with an inverting voltage nearly half that of the power supply with a gain of 9 at VDD = 100 V. 2012 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2013. Copyright

The influence of electron deficient unit and interdigitated packing shape of new polythiophene derivatives on organic thin-film transistors and photovoltaic cells

A series of new polythiophene derivatives containing a thiazole ring as an electron deficient unit were successfully synthesized via Stille coupling reactions. Synthesized polymers were classified into two types (H-shape packing and A-shape packing) based on their interdigitated packing structure induced by different side chain configurations. The thiophene derivatives that contained a thiazole unit (PT50Tz50, PTz100, and PTTz) exhibited much better thermal stability than did the full thiophene polymers (PT100 and PTT). The polymers containing the thiazole unit (PTz100 and PTTz) showed a red-shifted absorption spectrum with clear vibronic structure. In addition, the XRD and AFM results showed that the polymers containing the thiazole unit and interdigitated H-shape exhibited much better ordered and connected intermolecular structures than did other polymers. The improved intermolecular ordering and surface morphologies directly facilitated charge carrier transport in thin film transistor (TFT) devices, without introducing charge traps, and yielded higher solar cell performance. Among these polymers, the PTTz copolymer exhibited the best TFT performance (μ = 0.050 cm2 V-1 s-1, on/off ratio = 106, and Vth = -2 V) and solar cell performance (PCE = 1.39%, Jsc = 6.58 mA cm-2, and Voc = 0.58 V).

Bithiophene-imide-based polymeric semiconductors for field-effect transistors: Synthesis, structure-property correlations, charge carrier polarity, and device stability

Developing new high-mobility polymeric semiconductors with good processability and excellent device environmental stability is essential for organic electronics. We report the synthesis, characterization, manipulation of charge carrier polarity, and device air stability of a new series of bithiophene-imide (BTI)-based polymers for organic field-effect transistors (OFETs). By increasing the conjugation length of the donor comonomer unit from monothiophene (P1) to bithiophene (P2) to tetrathiophene (P3), the electron transport capacity decreases while the hole transport capacity increases. Compared to the BTI homopolymer P(BTimR) having an electron mobility of 10 -2 cm2 V-1 s-1, copolymer P1 is ambipolar with balanced hole and electron mobilities of ～10-4 cm2 V-1 s-1, while P2 and P3 exhibit hole mobilities of ～10-3 and ～10-2 cm2 V-1 s-1, respectively. The influence of P(BTimR) homopolymer Mn on film morphology and device performance was also investigated. The high Mn batch P(BTimR)-H affords more crystalline film microstructures; hence, 3- increased electron mobility (0.038 cm 2 V-1 s-1) over the low Mn one P(BTimR)-L (0.011 cm2 V-1 s-1). In a top-gate/bottom-contact OFET architecture, P(BTimR)-H achieves a high electron mobility of 0.14 cm2 V-1 s-1, only slightly lower than that of state-of-the-art n-type polymer semiconductors. However, the high-lying P(BTimR)-H LUMO results in minimal electron transport on exposure to ambient. Copolymer P3 exhibits a hole mobility approaching 0.1 cm2 V-1 s-1 in top-gate OFETs, comparable to or slightly lower than current state-of-the-art p-type polymer semiconductors (0.1-0.6 cm 2 V-1 s-1). Although BTI building block incorporation does not enable air-stable n-type OFET performance for P(BTimR) or P1, it significantly increases the OFET air stability for p-type P2 and P3. Bottom-gate/top-contact and top-gate/bottom-contact P2 and P3 OFETs exhibit excellent stability in the ambient. Thus, P2 and P3 OFET hole mobilities are almost unchanged after 200 days under ambient, which is attributed to their low-lying HOMOs (>0.2 eV lower than that of P3HT), induced by the strong BTI electron-withdrawing capacity. Complementary inverters were fabricated by inkjet patterning of P(BTimR)-H (n-type) and P3b (p-type).

CONJUGATED MONOMERS AND POLYMERS AND PREPARATION AND USE THEREOF

Disclosed are new conjugated compounds (e.g., monomers and polymers) that include ladder-type moieties which can be used for preparing semiconducting materials. Such conjugated compounds can exhibit high n-type carrier mobility and/or good current modulat