5,12-Bis(phenylethynyl)naphthacene

• CAS: 18826-29-4
• Catalog Number: ACM18826294
• Category: Main Products
• Molecular Weight: 428.5
• Molecular Formula: C34H20
• Description: 5,12-Bis(phenylethynyl)naphthacene (5,12-BPEN) is a synthetic organic compound belonging to the class of naphthalene derivatives. It is a derivative of naphthalene and is composed of two phenylethynyl groups connected to a central naphthalene ring.; 5,12-BPEN has been studied extensively for its potential applications in scientific research and has been found to have a range of biochemical and physiological effects. b experiments, and its potential future directions.
• Synonyms: 5,12-Bis(phenylethynyl)tetracene
• SMILES: C1=CC=C(C=C1)C#CC2=C3C=CC=CC3=C(C4=CC5=CC=CC=C5C=C42)C#CC6=CC=CC=C6
• InChI: InChI=1S/C34H20/c1-3-11-25(12-4-1)19-21-31-29-17-9-10-18-30(29)32(22-20-26-13-5-2-6-14-26)34-24-28-16-8-7-15-27(28)23-33(31)34/h1-18,23-24H
• InChI Key: OUHYGBCAEPBUNA-UHFFFAOYSA-N
• Boiling Point: 683.7ºC at 760mmHg
• Melting Point: 248 °C
• Flash Point: 369.5 ºC
• Density: 1.25 g/mL
• Appearance: White to Off-White powder
• Application: 5,12-Bis(phenylethynyl)naphthacene has been studied extensively for its potential applications in scientific research. It has been used in the study of the structure and function of proteins, as well as in the study of the interactions between proteins and other molecules. It has also been used in the study of DNA and RNA, as well as in the study of the structure and function of cells. Additionally, 5,12-Bis(phenylethynyl)naphthacene has been used in the study of the role of lipids in cell membranes and in the study of the role of enzymes in metabolic pathways.
• Storage: Store at 2-8 ℃
• EC Number: 242-605-4
• Exact Mass: 428.157
• Hazard Codes: Xi: Irritant
• HTS Code: 2902909090
• MDL Number: MFCD00012052
• Refractive Index: 1.784
• Vapor Pressure: 9.02E-18mmHg at 25°C
• XLogP3: 7.9458

Case Study

5,12-Bis(phenylethynyl)naphthacene Used for the Efficient Synthesis of Unsymmetrical 5,12-Diethynyltetracene Derivatives

Iwanaga T,et al. Synthesis, 2015, 47(24): 3997-4007.

Unsymmetrical 5,12-diethynyltetracene derivatives were synthesized from tetracenequinone by the addition of two types of ethynyllithium reagents, followed by reductive aromatization with SnCl2-. These three-step reactions could be integrated into a one-pot process to give unsymmetrically substituted 5,12-diethynyltetracene derivatives in moderate yields. Some unsymmetrical 5,12-bis(phenylethynyl)tetracene derivatives were synthesized from 5-ethynyl-12-phenylethynyltetracene and iodobenzenes by Sonogashira coupling. This integrated process was applied to the synthesis of a π-extended tetracene dimer.

Ultrafast Singlet Fission and High Triplet Yield of 5,12-Bis(phenylethynyl)naphthacene (BPET) Thin Films for Photovoltaic Applications

Nandi, Amitabha, et al. The Journal of Physical Chemistry C 125.5 (2021): 2583-2591

This study investigated the singlet fission (SF) properties of 5,12-bis(phenylethynyl)naphthacene (BPET), a tetracene derivative, in thin film form to evaluate its potential for organic solar cells. BPET thin films (~60 nm thick) were prepared via thermal vapor deposition, exhibiting a monoclinic crystal structure with mixed crystalline and amorphous phases. Steady-state and time-resolved optical studies revealed efficient SF: the singlet exciton lifetime was reduced from 7.38 ns (THF solution) to 1.2 ps (thin film), with >90% of singlet excitons undergoing ultrafast deactivation. Ultrafast transient absorption spectroscopy showed that singlet excitons relaxed to correlated triplet pairs within <200 fs, followed by free triplet generation in 1.2 ps. A minor slower SF component (17 ps) was attributed to the amorphous phase. Nanosecond flash photolysis confirmed long-lived triplets (~3.6 ms), and triplet yield was estimated at ~180%-exceeding 100% confirms efficient SF. Phenylethynyl substituents modified energy levels (S₁=1.98 eV, T₁=0.85 eV) to make SF exothermic, enhanced intermolecular coupling (0.29 eV red shift in absorption vs. tetracene's 0.23 eV), and broadened visible absorption (covering most of the solar spectrum). These studies demonstrate that BPET thin films exhibit ultrafast, high-yield SF with long-lived triplets, making them promising for singlet fission-based solar cells.The in vitro evaluation of BPET's SF properties was conducted through comprehensive optical and structural characterization. Thin films were prepared under high vacuum (1×10⁻⁶ mbar) with a deposition rate of 0.2-0.5 Å/s. Structural analysis included atomic force microscopy (AFM) for morphology, X-ray diffraction (XRD) for crystal structure, and coherence correlation interferometry for thickness. Steady-state UV-visible absorption and photoluminescence spectra were recorded to assess spectral shifts and emission quenching. Time-resolved measurements included fluorescence upconversion (200 fs resolution) for ultrafast singlet decay, transient absorption spectroscopy for exciton dynamics, and nanosecond flash photolysis for triplet lifetime. Triplet yield was calculated via the singlet depletion method using ground state bleach and triplet-triplet absorption signals. All experiments were performed at room temperature, with statistical analysis of kinetic fitting parameters (multiexponential fits) to resolve SF components.

Co-assembly of 5,12-Bis(phenylethynyl)naphthacene (BN) with 9,10-Bis(phenylethynyl)anthracene (BA) into Organic Alloy Helices and Core-Shell Structures

Lei, Yilong, et al. Nature Communications 9.1 (2018): 4358

This study investigated the co-assembly behavior of 5,12-bis(phenylethynyl)naphthacene (BN), a twisted π-conjugated semiconductor, with planar 9,10-bis(phenylethynyl)anthracene (BA) to form organic alloy and core-shell structures. BN and BA were co-assembled via a liquid-phase route by injecting THF solutions into ethanol/water mixtures, with morphologies controlled by BA/BN molar ratio and solvent composition. At a 2:1 BA/BN molar ratio and 4:1 ethanol/water volume ratio, homogeneous (BA)₀.₇₂(BN)₀.₂₈ alloy helices were formed, featuring left- and right-handed configurations (width ~10 μm, length tens of μm). Structural analysis (XRD, ¹H NMR, TEM) confirmed BN molecules randomly occupied BA lattice sites, forming a single-crystalline alloy with π-π stacking distances of 3.367-3.466 Å. The alloy exhibited tunable luminescence (orange-red to NIR) due to 100% efficient energy transfer from BA to BN. Additionally, BA@(BA)ₓ(BN)₁₋ₓ core-shell structures were fabricated via solute exchange: BA tubes served as cores, with (BA)ₓ(BN)₁₋ₓ alloy epitaxially grown as shells (lattice mismatch f=2.28%), showing dual-color emission (yellow core, red shell). These studies demonstrate that BN's structural compatibility with BA enables controlled co-assembly into functional alloy helices and core-shell structures, promising for optoelectronic applications.The in vitro co-assembly and characterization were conducted through systematic morphological and structural analyses. BA and BN microtubes were first synthesized individually, then co-assembled by varying molar ratios (100:1 to 1:1) and solvent compositions (ethanol/water volume ratios 17:3 to 13:7). Morphologies were visualized via SEM and TEM, with crystallinity confirmed by XRD and selected-area electron diffraction (SAED). Alloy composition was determined by ¹H NMR integration of characteristic peaks. Optical properties (absorption, photoluminescence) were measured via spectrofluorometry and fluorescence microscopy (excitation at 430-460 nm and 510-550 nm). Core-shell structures were prepared by mixing BA tubes with saturated (BA)₀.₇₂(BN)₀.₂₈ supernatant, with shell thickness tuned by supernatant volume. All experiments were performed at room temperature, with statistical analysis of structural parameters (stacking distances, lattice mismatch) and optical data (emission wavelengths, energy transfer efficiency).

Custom Q&A

What is the molecular formula of 5,12-Bis(phenylethynyl)naphthacene?

The molecular formula is C34H20.

What is the molecular weight of 5,12-Bis(phenylethynyl)naphthacene?

The molecular weight is 428.5 g/mol.

What is the IUPAC name of 5,12-Bis(phenylethynyl)naphthacene?

The IUPAC name is 5,12-bis(2-phenylethynyl)tetracene.

What is the InChI of 5,12-Bis(phenylethynyl)naphthacene?

The InChI is InChI=1S/C34H20/c1-3-11-25(12-4-1)19-21-31-29-17-9-10-18-30(29)32(22-20-26-13-5-2-6-14-26)34-24-28-16-8-7-15-27(28)23-33(31)34/h1-18,23-24H.

What is the InChIKey of 5,12-Bis(phenylethynyl)naphthacene?

The InChIKey is OUHYGBCAEPBUNA-UHFFFAOYSA-N.

What is the canonical SMILES of 5,12-Bis(phenylethynyl)naphthacene?

The canonical SMILES is C1=CC=C(C=C1)C#CC2=C3C=CC=CC3=C(C4=CC5=CC=CC=C5C=C42)C#CC6=CC=CC=C6.

What is the CAS number of 5,12-Bis(phenylethynyl)naphthacene?

The CAS number is 18826-29-4.

What is the European Community (EC) number of 5,12-Bis(phenylethynyl)naphthacene?

The European Community (EC) number is 242-605-4.

What is the UNII of 5,12-Bis(phenylethynyl)naphthacene?

The UNII is MKZ3D4QP9D.

What is the molecular weight of 5,12-Bis(phenylethynyl)naphthacene computed by PubChem?

The molecular weight computed by PubChem is 428.5 g/mol.