444579-42-4

Basic information

• Product Name: tributyl(4-hexylthiophen-2-yl)stannane
• Synonyms: tributyl(4-hexylthiophen-2-yl)stannane;IN1481, Tributyl(4-hexylthiophen-2-yl)stannane
• CAS NO: 444579-42-4
• Molecular Formula: C22H42SSn
• Molecular Weight: 457.34388
• EINECS: -0
• Mol File: 444579-42-4.mol

Chemical Properties

• Boiling Point: 136-138 °C(Press: 4 Torr)
• Appearance: /
• CAS DataBase Reference: tributyl(4-hexylthiophen-2-yl)stannane(CAS DataBase Reference)
• NIST Chemistry Reference: tributyl(4-hexylthiophen-2-yl)stannane(444579-42-4)
• EPA Substance Registry System: tributyl(4-hexylthiophen-2-yl)stannane(444579-42-4)

Safety Data

• Hazardous Substances Data: 444579-42-4(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
Tributyl(4-hexylthiophen-2-yl)stannane is used as a reagent in organic synthesis for its high thermal stability and solubility in common organic solvents, making it suitable for a wide range of synthetic applications.
Used in Optoelectronic Material Production:
Tributyl(4-hexylthiophen-2-yl)stannane is used as a precursor in the production of organic optoelectronic materials due to its ability to form stable and efficient interfaces with other organic materials.
Used in Electronic Device Fabrication:
In the Electronics Industry, tributyl(4-hexylthiophen-2-yl)stannane is used as a component in the fabrication of electronic devices such as organic light-emitting diodes (OLEDs) and organic solar cells, where its properties contribute to the performance and efficiency of these devices.

Upstream product

• 1461-22-9 tri-n-butylstannyl chloride 
• 1693-86-3 3-hexylthiophene 
• 111-25-1 1-bromo-hexane 
• 109-72-8 n-butyllithium 
• 7646-78-8 tin(IV) chloride 
• 1461-22-9 tributyltin chloride 

Downstream Products

• 761416-46-0 4,7-bis-(4-hexyl-thiophen-2-yl)-benzo[1,2,5]thiadiazole 
• 1438278-18-2 5-(7-(5-(4-(diphenylamino)phenyl)-4-hexylthiophen-2-yl)-2-hexyl-2H-benzo[d][1,2,3]triazol-4-yl)-3-hexylthiophene-2-carbaldehyde 
• 1438278-23-9 2-cyano-3-(5-{7-[5-(4-diphenylaminophenyl)-4-hexyl-thiophen-2-yl]-2-hexyl-2H-benzotriazol-4-yl}-3-hexylthiophen-2-yl)acrylic acid 
• 1526919-74-3 C₂₃H₂₄N₄O₂SSe 
• 1623149-57-4 2-(2-ethylhexyl)-5,7-bis(4-hexylthiophen-2-yl)benzo[1,2-b:4,5-c']dithiophene-4,8-dione 
• 1450590-76-7 4,7-di(4-hexyl-5-bromothiophen-2-yl)-5,6-difluorine-2,1,3-benzothiadiazole 
• 135926-93-1 3,4'-dihexyl-2,2'-bithiophene 
• 1429062-29-2 C₈₂H₈₆N₄S₅ 

Relevant articles and documents

D-A-D structured selenadiazolesbenzothiadiazole-based near-infrared dye for enhanced photoacoustic imaging and photothermal cancer therapy

Near-infrared (NIR) small molecular organic dyes as photothermal agents for cancer photothermal therapy (PTT) have attracted considerable research attention. Herein, two donor-acceptor-donor (D-A-D) structured NIR dyes, BBTT and SeBTT, are rationally designed, where the only difference is one heteroatom within the acceptor unit varying from sulfur to selenium (Se). More importantly, SeBTT NPs exhibit stronger NIR absorbance and higher photothermal conversion efficiency (PTCE ≈ 65.3%). In vivo experiments illustrate that SeBTT NPs can be utilized as a high contrast photoacoustic imaging (PAI) agent, and succeed in tumor suppression without noticeable damage to main organs under NIR photoirradiation. This study presents an effective molecular heteroatom surgery strategy to regulate the photothermal properties of NIR small molecules for enhanced PAI and PTT.

Altering Electronic and Optical Properties of Novel Benzothiadiazole Comprising Homopolymers via π Bridges

Four novel benzo[c][1,2,5]thiadiazole comprising monomers namely 5-fluoro-6-((2-octyldodecyl)oxy)-4,7-di(thiophen-2-yl)benzo[c][1,2,5]thiadiazole (TBTT), 5-fluoro-4,7-bis(4-hexylthiophen-2-yl)-6-((2-octyldodecyl)oxy)benzo[c][1,2,5]thiadiazole (HTBTHT), 5-fluoro-4,7-di(furan-2-yl)-6-((2-octyldodecyl)oxy)benzo- [c][1,2,5]thiadiazole (FBTF), and 5-fluoro-6-((2-octyldodecyl)oxy)-4,7-bis(thieno[3,2-b]thiophen-2-yl)benzo[c][1,2,5]thiadiazole (TTBTTT) were designed, and synthesized successfully via Stille polycondensation reaction. The structural characterizations of the monomers were performed by 1H and 13C NMR spectroscopy and High Resolution Mass Spectroscopy (HRMS). The monomers were then electropolymerized in a three electrode cell system via cyclic voltammetry. The electrochemical, and spectroelectrochemical characterization of the polymers were reported in detail. Besides, theoretical calculations were performed to elucidate observed experimental properties. According to the cyclic voltammogram of the polymers, HOMO and LUMO energy levels were calculated as -5.68 eV/-3.91 eV, -5.71 eV/-3.72 eV, -5.61 eV/-4.04 eV, and -5.51 eV/-3.71 eV and the electronic band gaps were 1.77 eV, 1.99 eV, 1.57 eV, and 1.80 eV for PTBTT, PHTBTHT, PFBTF, and PTTBTTT, respectively.

Synthesis of selenophene substituted benzodithiophene and fluorinated benzothiadiazole based conjugated polymers for organic solar cell applications

A series of alternating conjugated copolymers which contain selenophene modified benzodithiophene and fluorine bearing benzothiadiazole have been synthesized via Stille polycondensation reaction to investigate the effect of the number of fluorine atoms substituted to the benzothiadiazole. Three different polymers, PBDTSe-BT, PBDTSe-FBT and PBDTSe-FFBT, were reported and their electrochemical, spectroelectrochemical, and photovoltaic behaviors were examined. Density functional theory calculations were performed on model tetramer structures to shed light on how substituting the fluorine atom to the acceptor building block affects the structural, electronic and optical properties of the polymers. The results of computational studies were compared with experimental studies. The structure adjustment accomplished by fluorine substitution on the benzothiadiazole moiety reveals an influence on the electronic structure of polymers with a more negative HOMO energy level. A high VOC for the resulting photovoltaic device was examined for PBDTSe-FFBT. Difluorinated polymer PBDTSe-FFBT:PC71BM organic solar cell exhibited the highest photovoltaic performance of 2.63% with JSC of 7.24 mA cm-2, VOC of 0.72 V and FF of 50.6%. PBDTSe-BT:PC71BM revealed the best PCE as 2.39%, and the device reached the highest efficiency up to 1.68% for PBDTSe-FBT:PC71BM.

Fluorene ring group-containing non-condensed ring organic small molecular material and preparation method and application thereof

The invention relates to a fluorene ring group-containing non-condensed ring organic small molecular material and a preparation method and an application thereof. 2, 7-di(4, 4, 5, 5-tetramethyl-1, 3-dioxo-2-borane)-9, 9-dioctyl fluorene is used as a central core unit, and a thiophene unit is introduced to enhance [pi] conjugation of a molecular main chain, on this basis, benzothiadiazole is introduced to increase the electron deficiency capacity of the obtained molecule, thiophene units are connected to the two sides to expand conjugation and finally reduce the energy band gap of the molecule, side chains on thiophene can improve the solubility of the molecule, and fluorine-containing cyanoindanone units are connected to the two ends to form effective charge transfer in the whole molecule.

Planar and twisted molecular structure leads to the high brightness of semiconducting polymer nanoparticles for NIR-IIa fluorescence imaging

Semiconducting polymer nanoparticles (SPNs) emitting in the second near-infrared window (NIR-II, 1000-1700 nm) are promising materials for deep-tissue optical imaging in mammals, but the brightness is far from satisfactory. Herein, we developed a molecular design strategy to boost the brightness of NIR-II SPNs: structure planarization and twisting. By integration of the strong absorption coefficient inherited from planar π-conjugated units and high solid-state quantum yield (φPL) from twisted motifs into one polymer, a rise in brightness was obtained. The resulting pNIR-4 with both twisted and planar structure displayed improved φPL and absorption when compared to the planar polymer pNIR-1 and the twisted polymer pNIR-2. Given the emission tail extending into the NIR-IIa region (1300-1400 nm) of the pNIR-4 nanoparticles, NIR-IIa fluorescence imaging of blood vessels with enhanced clarity was observed. Moreover, a pH-responsive poly(β-amino ester) made pNIR-4 specifically accumulate at tumor sites, allowing NIR-IIa fluorescence image-guided cancer precision resection. This study provides a molecular design strategy for developing highly bright fluorophores.

Highly fluorescent triazolopyridine-thiophene D-A-D oligomers for efficient pH sensing both in solution and in the solid state

Conjugated fluorophores have been extensively used for fluorescence sensing of various substances in the field of life processes and environmental science, due to their noninvasiveness, sensitivity, simplicity and rapidity. Most existing conjugated fluorophores exhibit excellent light-emitting performance in dilute solutions, but their properties substantially decrease or even completely vanish due to severe aggregation quenching in the solid state. Herein, we synthesize a series of triazolopyridine-thiophene donor-acceptor-donor (D-A-D) type conjugated molecules with high absolute fluorescence quantum yields (ΦF) ranging from 80% to 89% in solution. These molecules also show unusual light-emitting properties in the solid state with ΦF of up to 26%. We find that owing to the protonation-deprotonation process of the pyridine ring, these compounds display obvious changes in both fluorescence wavelength and intensity upon addition of acids, and these changes can be readily recovered by the successive introduction of bases. By harnessing this phenomenon, we further show that these fluorophores can be employed for efficient and reversible fluorescence sensing of hydrogen ions in a broad pH range (0.0-7.0). With the fabrication of pH testing papers and ink-printed complex patterns including butterflies and letters on substrates, we demonstrate the application of such sensors to fluorescence indication or solid state pH detection for real samples such as volatile acidic/basic gas and water-quality analysis.

Selenium-containing near-infrared organic semiconductor as well as preparation method and application thereof

The invention relates to a selenium-containing near-infrared organic semiconductor as well as a preparation method and application of the organic semiconductor to photothermal therapy of tumor. The organic semiconductor is characterized in that selenium atoms are introduced into benzothiadiazole units; the selenium atoms have high polarizability; the spectrum moves to a long-wavelength direction;through the organic semiconductor, an organic nano material with absorption wavelength (an ultraviolet absorption wavelength reaches up to 906nm, and a fluorescence emission wavelength reaches up to 1040nm) in a near-infrared area is obtained by a re-precipitation method; the nano reagent has high photothermal conversion efficiency, excellent water dispersibility, excellent tumor tissue targetingproperty and high biological compatibility, can be applied to therapy of tumor cells and living organisms, and is capable of effectively inhibiting the growth of the tumor cells and effectively inhibiting metastasis of tumor cells so as to achieve the photothermal therapy effect of the tumor, so that the nano reagent has great application prospects in the field of tumor therapy.

A fast response of nitric oxide near-infrared probe and its preparation and biological applications (by machine translation)

The invention relates to a fast response of nitric oxide near-infrared probe and its preparation and biological application, the structure shown in formula (I), which belongs to the field of organic fluorescent probe. This invention is designed and has synthesized a kind of fast response of the near-infrared nitric oxide probe. The probe is after NO response with near-infrared emission. In vitro experimental study shows that, probe and NO fast reaction speed. In the physiological conditions (pH 7.4) next, probe stability, and to NO has higher sensitivity, selectivity and interference. Biological experimental study shows that, probe not only can be applied to the cell in the level of endogenous NO detection, can also be applied to PD cell and Drosophila brain model in NO level of detection. These results indicate that, the probe has a relatively high specificity, selectivity, stability, which may be applied to the early diagnosis of Parkinson's disease. (by machine translation)

Alkyl chain thienyl seaver alkali and its synthesis method (by machine translation)

This invention relates to alkyl chain thienyl Sievert alkali and synthetic method, thienyl Sievert alkali of the alkyl chain of the formula Alkyl chain thienyl Sievert alkali preparation method: (1) by the alkyl chain thiophene synthetic intermediates I;

Syntheses and photovoltaic properties of 6-(2-thienyl)-4H-thieno[3,2-b]indole based conjugated polymers containing fluorinated benzothiadiazole

In this report, a series of copolymers based on 6-(2-thienyl)-4H-thieno[3,2-b]indole (TTI) as an electron-rich unit and fluorinated DTBT as an electron-deficient unit were synthesized, namely PTTIF1 and PTTIF2, and applied to photovoltaic devices. TTI unit was coupled with fluorinated DTBT to utilize the merit of introduction of fluorine atom leading to the lowering of the HOMO energy level while keeping high planarity of the conjugated backbone. The synthesized copolymers show a noticeable change in HOMO energy levels as compared with non-fluorinated polymer (PTTIDTBT-h). Optimized photovoltaic devices of PTTIF2 exhibited power conversion efficiency of 4.36% with decent JSC and FF values, which can be explained by the higher charge transporting ability of PTTIF2 with preferable face-on crystallite population than PTTIF1 in grazing incident wide-angle X-ray scattering (GIWAXS).