910467-75-3

Basic information

• Product Name: 4-((4-((Trimethylsilyl)ethynyl)-phenyl)ethynyl)phenol
• Synonyms: 4-((4-((Trimethylsilyl)ethynyl)-phenyl)ethynyl)phenol;4-[2-[4-[2-(trimethylsilyl)ethynyl]phenyl]ethynyl]Phenol
• CAS NO: 910467-75-3
• Molecular Formula: C₁₉H₁₈OSi
• Molecular Weight: 290.43112
• Mol File: 910467-75-3.mol

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 4-((4-((Trimethylsilyl)ethynyl)-phenyl)ethynyl)phenol(CAS DataBase Reference)
• NIST Chemistry Reference: 4-((4-((Trimethylsilyl)ethynyl)-phenyl)ethynyl)phenol(910467-75-3)
• EPA Substance Registry System: 4-((4-((Trimethylsilyl)ethynyl)-phenyl)ethynyl)phenol(910467-75-3)

Safety Data

• Hazardous Substances Data: 910467-75-3(Hazardous Substances Data)

Usage

Uses

Used in Materials Science:
4-((4-((Trimethylsilyl)ethynyl)-phenyl)ethynyl)phenol is utilized as a key component in the development of organic semiconductors due to its unique structure and properties that contribute to the advancement of electronic devices.
Used in Electronic Devices:
In the electronics industry, 4-((4-((Trimethylsilyl)ethynyl)-phenyl)ethynyl)phenol is employed as a constituent material for creating innovative electronic devices, leveraging its potential in enhancing the performance and functionality of such technologies.

Upstream product

• 2200-91-1 4-ethynylphenol 
• 134856-58-9 1-iodo-4-(trimethylsilylethynyl)benzene 
• 540-38-5 p-Iodophenol 

Relevant articles and documents

Systematic studies on photoluminescence of oligo(arylene-ethynylene)s: Tunability of excited states and derivatization as luminescent labeling probes for proteins

Functionalized oligo(phenylene-ethynylene)s (OPEs) with different conjugation lengths, p-X(C6H4C≡C) nSiMe3 (n = 1-4; X = NH2, NMe2, H) were synthesized by Sonogashira coupling of (phenylene-ethynylene)s and 1-iodo-4-(trimethylsilylethynyl)benzene, followed by desilylation of the p-substituted (trimethylsilylethynyl)benzenes with potassium hydroxide. The photoluminescent properties for the OPE series with different chain lengths and their solvatochromic responses were examined. The absorption maxima were red-shifted with increasing numbers of -(C6H4C≡C)- units (n), and a linear plot of the absorption energy maxima vs. 1/n was obtained for each series. The emission spectra in dichloromethane showed a broad and structureless band, the energies of which (in wavenumbers) also fit linearly with 1/n. Both the absorption and emission wavelength maxima of the NH2- and NMe2-substituted OPEs exhibited significant solvent dependence, whereas the parent OPEs (X = H) showed only minor shifts of the λmax values in different solvents. Substituent effects upon the photoluminescent characteristics of the OPEs and the tunability of the excited states were examined with the p-X(C6H4C≡C) nSiMe3 (n = 2, 3; X = NH2, NMe2, H, SMe, OMe, OH, and F) series. The H- and F-substituted counterparts exhibited high-energy vibronically structured emissions attributed to the 3(ππ*) excited states of the (arylene-ethynylene) backbone. For compounds bearing NH2 and NMe2 groups, a broad red-shifted emission with a remarkable Stokes shift from the respective absorption maximum was observed, which can be assigned to an n → π* transition. The n → π* assignment was supported by MO calculations on the model compounds p-X(C6H4C≡C) 2SiH3 (X = NH2, H). Functionalization of the oligo(arylene-ethynylene)s with the N-hydroxysuccinimidyl (NHS) moiety enabled covalent attachment of the fluorophore to HSA protein molecules. A series of fluorescent labels, namely p-X(C6H4C≡C) n-C6H4NHS, (n = 1, X = NH2, NMe 2, SMe, OMe, OH, F; n = 2, X = NH2, NMe2) and p-Me2NC6H4C≡C(C4H 2S)-C≡CC6H4NHS were synthesized, and their conjugates with HSA (human serum albumin) were characterized by MALDI-TOF mass spectrometry, UV/Vis absorption spectroscopy, and gel electrophoresis. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.