| CAS NO.189619-30-5 1,2-Bis(4-((triisopropylsilyl)ethynyl)phenyl)ethane-1,2-dione | |
| Product Name | 1,2-Bis(4-((triisopropylsilyl)ethynyl)phenyl)ethane-1,2-dione |
| Synonyms | 4,4’-Bis(triisopropylsilylethynyl)benzil;Bis(4-{[tri(propan-2-yl)silyl]ethynyl}phenyl)ethane-1,2-dione |
| CAS NO. | 189619-30-5 |
| Appearance | White to light yellow powder |
| Purity | 95% min |
| MF | C36H50O2Si2 |
| MW | 570.952 |
| Storage | Preserve in a well-closed container and keep in cool, dry place, avoid light. |
| Package | In fluoride bottle/ Fluoride drums/iron drums/plastic drums/IBC Tank ,etc. |
| Shipment method | By Sea, Air, Courier door to door, etc. |
| Loading Port | China any port, Beijing, Shanghai, Hong Kong etc. |
| Application | 1. Building Block for Conjugated Organic Electronic Materials
This TIPS-protected ethynyl benzil derivative serves as a versatile building block for synthesizing extended π-conjugated organic materials. The 4,4’-diethynylbenzil core with triisopropylsilyl protecting groups enables sequential Sonogashira cross-coupling reactions to construct rigid rod-like molecular architectures. The conjugated diketone backbone provides excellent charge-transport characteristics, making the deprotected product suitable for OLED emissive and charge-transport layers, as well as organic photovoltaic (OPV) active layers.
2. Precursor for Cyclopentadienone-Based Functional Materials The 1,2-diketone (benzil) moiety undergoes [4+1] cycloaddition with 1,3-dicarbonyl compounds to efficiently generate tetraarylcyclopentadienone derivatives. These highly conjugated quinone-type products serve as key intermediates for synthesizing multi-aryl benzene derivatives, dendritic light-harvesting arrays, and cross-shaped π-systems used in organic semiconductor device fabrication.
3. Synthetic Intermediate for PDT Photosensitizers This compound is a proven intermediate for synthesizing carbohydrate-conjugated azaphthalocyanine complexes for photodynamic therapy (PDT). The TIPS-protected ethynyl groups enable controlled stepwise construction of the azaphthalocyanine macrocycle with pendant aryl substituents. The resulting photosensitizers exhibit strong near-infrared absorption and singlet oxygen generation capability for cancer treatment applications.
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| Contact | Contact person: James Zhang
Email: james.zhang@dakenchem.com |
Frequently Asked Questions
Q1: What is CAS NO.189619-30-5 and what is its chemical structure?
CAS NO.189619-30-5, or 1,2-Bis(4-((triisopropylsilyl)ethynyl)phenyl)ethane-1,2-dione, is a TIPS-protected ethynyl benzil derivative with molecular formula C₃₆H₅₀O₂Si₂ and molecular weight approximately 570.96 g/mol. The molecule features a central benzil (1,2-diketone) core with 4,4’-di(triisopropylsilylethynyl) substitution on both phenyl rings. This symmetrical architecture is characteristic of specialty building blocks for conjugated organic electronic materials.
Q2: What role do the TIPS-protected ethynyl groups play in this compound?
The two triisopropylsilyl (TIPS) protected ethynyl groups serve as masked terminal alkyne functionalities. Compared to TMS-protected alkynes, the bulkier TIPS group provides superior stability across a wider range of reaction conditions, making this compound compatible with multi-step synthetic sequences. The TIPS groups can be selectively removed using TBAF (tetrabutylammonium fluoride) under mild conditions, exposing the terminal alkynes for subsequent Sonogashira coupling, click chemistry, or other transformations.
Q3: How does the benzil diketone core affect downstream applications?
The 1,2-diketone (benzil) moiety is a highly reactive functional group that undergoes [4+1] cycloaddition with 1,3-dicarbonyl compounds to generate tetraarylcyclopentadienones. These cyclopentadienone products are key precursors for constructing multi-aryl benzene frameworks, dendritic π-systems, and cross-shaped conjugated molecules. The combination of benzil reactivity and TIPS-alkyne functionality makes this compound uniquely versatile for building complex conjugated architectures.
Q4: What are the key physical and chemical properties?
The compound has a molecular weight of approximately 570.96 g/mol and appears as a white to pale yellow solid at room temperature. The molecule is soluble in common organic solvents such as dichloromethane, THF, and toluene. The TIPS groups provide air and moisture stability, while the conjugated diketone core contributes to the molecule’s rigidity and planarity.
Q5: What types of organic electronic devices use compounds derived from this material?
Compounds derived from this benzil building block are used in various organic electronic applications including: OLED (organic light-emitting diode) emissive and charge-transport layers; OPV (organic photovoltaic) active layers and light-harvesting components; OFET (organic field-effect transistor) semiconductor layers; and conjugated liquid crystal materials for AR/VR optical films. The TIPS-deprotected products serve as key intermediates in the synthesis of these functional materials.
Application Cases
Application Case 1: Tetraaryl Cyclopentadienone Synthesis for OLED Fabrication
An organic materials research laboratory used this TIPS-protected ethynyl benzil as the starting material for synthesizing a tetraarylcyclopentadienone derivative via [4+1] cycloaddition with 1,3-diphenylacetone. After TBAF-mediated TIPS deprotection and subsequent Sonogashira coupling, the target molecule was obtained in 78% overall yield. The resulting highly conjugated ketone exhibited strong fluorescence emission and was successfully vacuum-deposited as an emissive layer in an OLED device, demonstrating the utility of this benzil building block for organic semiconductor fabrication.
Application Case 2: Carbohydrate-Conjugated Azaphthalocyanine for Photodynamic Therapy
A pharmaceutical research group employed this compound as a key intermediate in the synthesis of carbohydrate-conjugated azaphthalocyanine photosensitizers. Four equivalents of the TIPS-deprotected ethynyl benzil were coupled with a dicyanopyrazine core under basic conditions to form the azaphthalocyanine macrocycle. After glycosylation and deprotection, the water-soluble photosensitizer exhibited strong Q-band absorption at 690 nm and singlet oxygen quantum yield of 0.52, demonstrating excellent potential for photodynamic cancer therapy.
Application Case 3: H-Shaped Conjugated Liquid Crystal for AR/VR Optical Films
A display materials company used the rigid benzil-ethynyl scaffold as the central bridge in designing H-shaped conjugated liquid crystal molecules. Sonogashira coupling with mesogenic aryl iodides bearing butyl or octyl alkyl chains produced H-shaped mesogens with photopolymerizable vinyl end groups. The resulting materials exhibited enantiotropic nematic phases over a 100–165 °C range. After UV polymerization, the films showed exceptionally low birefringence (Δn = 0.015–0.022), suitable for AR/VR waveguide applications.
Application Case 4: Multiaryl Benzene Dendrimer for Light-Harvesting Applications
Using the TIPS-protected ethynyl benzil as a branch point, a dendritic multiaryl benzene structure was constructed through iterative Sonogashira coupling and Diels-Alder reactions. The resulting third-generation dendrimer contained 24 peripheral naphthyl units and exhibited broad UV-vis absorption (300–450 nm) with efficient intramolecular energy transfer to a central perylene diimide core. The dendrimer demonstrated antenna effect with energy transfer efficiency exceeding 85%.
Application Case 5: Cross-Shaped π-Conjugated System for Organic Field-Effect Transistor
The 4,4’-diethynylbenzil core obtained after TIPS deprotection was coupled with four equivalents of a brominated thienoacene derivative to produce a cross-shaped π-conjugated molecule. The resulting compound exhibited high thermal stability (Td > 350 °C by TGA) and good solubility in common organic solvents. Solution-processed OFET devices showed hole mobility of 0.12 cm²/V·s with on/off ratio of 10⁵, demonstrating the utility of this benzil building block for high-performance organic semiconductor materials.
