190843-93-7

Usage

Uses

Used in Chemical Synthesis Industry:
4,5,9,10-Pyrenetetrone, 2,7-bis(1,1-dimethylethyl)is used as a chemical intermediate for the production of dyes, pigments, and other organic compounds. Its enhanced stability and solubility due to the presence of tert-butyl groups make it a valuable building block in organic synthesis.
Used in Organic Electronics:
4,5,9,10-Pyrenetetrone, 2,7-bis(1,1-dimethylethyl)has been studied for its potential use in organic electronics, where its unique properties may contribute to the development of new electronic devices and materials.
Used as a Fluorescent Probe:
4,5,9,10-Pyrenetetrone, 2,7-bis(1,1-dimethylethyl)has been investigated for its potential use as a fluorescent probe for detecting DNA damage, which could have applications in molecular biology and diagnostics.

Upstream product

• 704860-92-4 2,7-di-tert-butyl-4,5-dihydropyrene-4,5-dione 
• 24300-91-2 2,7-di-tertbutylpyrene 
• 78751-86-7 2,7-di-tert-butyl-1-bromopyrene 
• 129-00-0 pyrene 
• 102587-98-4 2,7-dibromo-4,5,9,10-tetrahydropyrene 
• 76466-34-7 2,7-di-tert-butyl-4,5,9,10-tetrabromopyrene 
• 190843-91-5 2,7-di-tert-butyl-4,5,9,10-tetramethoxy-pyrene 

Downstream Products

• 1033319-19-5 C₁₀₄H₁₂₆N₈O₄ 
• 1033319-23-1 C₆₄H₇₄N₄O₄ 
• 1033318-93-2 C₁₀₀H₁₂₆N₄O₄ 
• 1033318-98-7 C₆₂H₇₄N₂O₄ 
• 1226759-41-6 C₆₄H₅₈N₈O₈S₄ 

Relevant academic research and scientific papers

Lateral extension induces columnar mesomorphism in crucifix shaped quinoxalinophenanthrophenazines This paper is dedicated to Professor Makhlouf J. Haddadin on the occasion of his 80th birthday and 50 years of outstanding service to the American University of Beirut

Reported here is the columnar mesomorphism of board shaped dyes based on quinoxalino[2′,3′:9,10]phenanthro[4,5-abc]phenazine (TQPP) derivatives that was induced by an increase in lateral bulk. TQPP derivatives with protons, tert-butyl and 4-tert-butyl-phenyl groups in positions 2 and 11 are compared, as well as dodecylthio, dodecyloxy, phytanylthio, and phytanyloxy side-chains. Only derivatives with 4-tert-butyl-phenyl groups display columnar liquid crystal phases over wide ranges of temperature while all other TQPPs are not liquid crystalline except for the compound with tert-butyl groups and phytanyloxy side-chains that shows a Colr mesophase over a temperature range of 26 °C. The sole attachment of phytanyl groups does not effectively induce columnar mesophases. However, the lateral attachment of bulky groups to the TQPP core induces columnar mesomorphism because of the in-plane aspect ratio decrease and the favored twisted or helical π-stacking of the molecules in columns rather than the parallel co-planar packing.

Synthesis and configurational character study of novel structural isomers based on pyrene-imidazole

Isomers provide more possibilities for the structure of organic compounds. Molecular structures determine their corresponding properties, therefore the intrinsic relationship between structure and properties of isomers is of great research value. Isomers with a stable structure and excellent performance possess more potential for development and application. In this paper, we design and synthesize structural isomers with different molecular symmetries based on the asymmetric structure of imidazole and the symmetrical structure of pyrene. Isomers with stable molecular structures can be obtained by a simple and efficient “one-pot” reaction, involving axisymmetric configuration and centrosymmetric configuration. Using this “click-like” reaction, the structure of target molecules is controllable and adjustable. Furthermore, the effect of molecular configurations on molecular stacking of crystal is studied. The variation of the optical and thermal properties, the optimized structures, and orbital distributions of isomers depends on different molecular geometry with different symmetry, which are revealed by crystallographic analysis. This present strategy provides an efficient synthetic method for the design and synthesis of structural isomers based on pyrene-imidazole.

Synthesis and binding investigations of novel crown-ether derivatives of phenanthro[4,5- abc ]phenazine and quinoxalino[2′,3′:9,10] phenanthro[4,5- abc ]phenazine

The synthesis and binding investigation of novel crown-ether derivatives of phenanthro[4,5-abc]phenazine and quinoxalino[2′,3′:9,10] phenanthro[4,5-abc]phenazine sensors are reported. The binding studies of these sensors with an array of alkali and alkaline-earth metals are exploited using UV-vis, fluorescence and nuclear magnetic resonance spectroscopies. 2013

Suppressing aggregation in a large polycyclic aromatic hydrocarbon

With the approach presented herein, a large aromatic π-system is synthesized, which shows extraordinarily high solubility and an effective suppression of aggregation. This was due to a distortion of the aromatic core by bulky tert-butyl groups and the sol

Synthesis and metal-binding studies of a novel pyrene discotic

The synthesis of a novel bis-crown quinoxalino[2′,3′:9,10]phenanthro[4,5-abc]phenazine discotic and its binding properties to a series of alkali and alkaline-earth metals is reported. A schematic representation of the binding equilibrium of the sensor to the metal is proposed. The binding constant of the sensor to barium(II) was estimated to be 1.4 × 104 M-1 based on 1H NMR studies.

Relationship Between Molecular Structure, Single crystal Packing and Self-Assembly Behavior: A Case Based on Pyrene Imide Derivatives

Development of new n-type one-dimensional (1D) self-assembly nanostructure and a clear understanding of the relationship between molecular structure and self-assembly behavior are important prerequisites for further designing and optimizing organic optoelectronic nanodevice. In this article, a series of n-type organic semiconductor materials based on pyrene imide were successfully synthesized through [4+2] cycloaddition reactions and their preliminary optical and electrochemical properties were studied. The simulated HOMO-LUMO bandgaps via DFT tallied with the experimental data well. The self-assembly of these materials showed needle or fiber-like morphologies, indicating that different conjugation degree or alkyl group had significant influence on their self-assembly behaviors. Furthermore, the single-crystal packing for these molecules were analyzed and it was found out that the changes of conjugated backbone and functional group would affect certain crystal lattice parameter significantly, such as the intermolecular packing distance and crystal size etc, which would further result in different self-assembly morphology.

Synthesis of Distorted Nitrogen-Doped Nanographenes by Partially Oxidative Cyclodehydrogenation Reaction

A series of partially fused N-doped nanographenes (2–4) are synthesized via the oxidative cyclodehydrogenation of oligoaryl-substituted dibenzo[e,l]pyrene (1), and five, six, and seven new C?C bonds are formed, respectively, implying stepwise C?C bond fusion and extended π-conjugation. Single-crystal X-ray diffraction analysis of compound 4 a revealed that the presence of sterically demanding groups hindered the formation of planar and fully fused nanographene in the oxidative cyclodehydrogenation reaction step. Optical study of compounds 2 to 4 showed that extended π-conjugation leads to a regular stepwise bathochromic shift in the absorption and emission spectra. Furthermore, the HOMO–LUMO gaps of these compounds exhibit a decrease as C?C bond formation proceeds. Thus, the optoelectronic properties of nanographenes are highly dependent on the formation of new C?C bonds in the molecular skeleton.

Sterically driven metal-free oxidation of 2,7-di-tert-butylpyrene

We disclose an unprecedented single-step metal-free green oxidation of 2,7-di-tert-butylpyrene selectively into either the corresponding 4,5-dione or 4,5,9,10-tetraone, two key building blocks used for organic optoelectronic applications using hypervalent

A tetraalkylated pyrene building block for the synthesis of pyrene-fused azaacenes with enhanced solubility

The synthesis and characterisation of a soluble pyrene-fused tetraazaoctacene derivative has been achieved by developing a key pyrene-based building block with four solubilising groups.

Dicyanopyrazine-containing fused aromatic molecules: Potential n-type materials for use in optoelectronic devices

Two dicyanopyrazine-containing aromatic compounds, pyrazino[2′, 3′:9,10]phenanthro[4,5-fgh]quinoxaline-5,6,12,13-tetracarbonitrile (PPQD) and pyrazino[2′,3′:9,10]phenanthro[4,5-fgh]quinoxaline-5,6,12,13- tetracarbonitrile,2,9-bis(1,1-dimethylethyl) (PPQB), which have remarkably high electron affinity and ionization potential, were synthesized and qualified as potential n-type materials for use in solar cells and organic light-emitting diodes.