2,2'-((1,2-ethenyl)bithiophene)- , CAS No.15332-30-6

CAS: 15332-30-6 Cat. No.: E1503847

Storage

Room temperature

Specifications

Condizioni di conservazione di stoccaggio

Room temperature

Application Protocols

No assay-specific or device fabrication protocols are provided for this item. General, literature-informed starting points for materials research include:

• Thin-film preparation: Dissolve at 5–20 mg/mL in chlorobenzene, toluene, or chloroform; filter (0.2 µm PTFE); spin-coat at 1000–3000 rpm; anneal 80–150 °C for 10–30 min. Adjust concentrations to match actual solubility (item-specific solubility not provided).
• Spectroscopy: Prepare ~10–50 µM solutions for UV–vis; use matched blanks to account for solvent absorption; protect from light during measurements.
• Crystallization: Slow evaporation from chlorobenzene/toluene mixtures or vapor diffusion (hexanes into chlorobenzene) to grow X-ray quality crystals if needed.

These are general suggestions; optimize for your instrumentation and end-use. For precise device stacks (OPV/OFET), consult the literature on TVT-based donors and adjust layer thickness, annealing, and solvent systems accordingly.

Biological Roles

This product is a conjugated organic material intended for materials science research. It is not designed for biological systems and has no established biological role.

General context (informational only):

• Thiophene rings occur in certain bioactive molecules, but extended bithiophene–vinylene scaffolds are primarily used in organic electronics and photonic materials rather than biochemistry.
• Conjugated thiophenes can interact with biomacromolecules via π–π stacking and hydrophobic interactions in research settings (e.g., fluorescent probes), yet such use requires bespoke functionalization for water compatibility and biocompatibility.

Research use note (from Product Data): For research use only. Not for use in humans or diagnostics.

Buffer Applications

Not typically applicable. This is a hydrophobic, conjugated small molecule used in materials science; it is not a buffering agent and is generally insoluble in water.

If dispersion in aqueous systems is desired for research:

• Consider surfactant-assisted dispersions, polymer wrapping, or nanoparticle formation with amphiphiles.
• Alternatively, introduce ionic or PEGylated substituents to render water compatibility (synthetic derivatization required).

Green Alternatives

Considerations for greener processing and synthesis (general guidance):

Greener processing solvents versus traditional:

• Aromatic processing
  • Traditional: Chlorobenzene, o-dichlorobenzene (excellent solvation, but higher toxicity/persistence)
  • Greener options: Anisole, toluene, mesitylene (lower toxicity; still effective for film casting)
• Chlorinated low-boilers
  • Traditional: DCM, chloroform (effective but hazardous)
  • Greener options: 2-MeTHF, CPME, ethyl acetate (where solubility permits); consider mixed-solvent systems
• Polar aprotics
  • Traditional: NMP, DMF (reprotoxic concerns)
  • Greener options: Cyrene, GBL, propylene carbonate (assess compatibility and drying)

Synthesis-stage improvements:

• Cross-coupling: Favor Suzuki couplings (boron reagents, aqueous workup) over Stille (organostannanes) to reduce tin waste.
• Catalyst economy: Employ ligand-optimized low-Pd loadings or Ni-catalysis where feasible; explore heterogeneous catalysts for easier recovery.
• Energy: Use continuous-flow heating or microwave to shorten times and reduce energy consumption.

Trade-offs:

• Solubility and film morphology can change significantly with greener solvents; re-optimize concentration, temperature, and drying/annealing profiles.
• Catalyst/ligand switches may affect regiochemistry and molecular weight (in polymerizations). Validate device metrics after any process change.

Pharmaceutical Uses

Not typically applicable. This compound is not an excipient or pharmacopeial ingredient and is supplied for materials science research.

Informational context (non-clinical):

• Thiophene fragments are present in some pharmaceutical actives, but extended bithiophene–vinylene frameworks are tailored for optoelectronic performance rather than formulation or drug delivery. Any exploration toward biomedical imaging or sensors would require additional functionalization, thorough toxicological evaluation, and is outside the scope of this product listing.

Physical Properties

Item-specific values:

• Melting point: Not specified for this item; refer to CoA/Spec Sheet.
• Boiling point: Not specified for this item; refer to CoA/Spec Sheet.
• Density: Not specified for this item; refer to CoA/Spec Sheet.
• Refractive index: Not applicable/unknown for a solid; Not specified for this item; refer to CoA/Spec Sheet.
• Solubility profile: Not specified for this item; refer to CoA/Spec Sheet.

General/literature-based expectations for conjugated bithiophene–vinylene motifs (guidance only, not product specifications):

• Physical state: Typically crystalline solids with orange–yellow coloration owing to extended conjugation.
• Solubility: Often sparingly soluble in aliphatic solvents; improved solubility in chlorinated (DCM, CHCl3, 1,2-dichloroethane), aromatic (toluene, chlorobenzene), and high-boiling polar aprotics (DMF, DMSO, NMP) depending on substitution.
• Thermal behavior: Conjugated oligothiophenes commonly exhibit high thermal stability and undergo sublimation or decomposition before classical distillation is practical. TGA onset (literature, related compounds) frequently >250 °C.
• Photophysics: UV–vis absorption typically in near-UV to visible (blue-green) with bathochromic shifts vs. 2,2′-bithiophene; exact λmax depends on geometry and substitution (not specified for this item).

LogP/pKa: Not typically defined for neutral π-conjugated solids; the compound is non-ionic and expected to be hydrophobic (literature generalization).

Quality and Grades

Item-specific grade/purity and stabilizers: Not specified for this item; refer to CoA/Spec Sheet.

Guidance for interpreting grades in conjugated small-molecule materials (general):

• Research grade: Suitable for exploratory synthesis and materials screening; typical for early device prototyping.
• Electronic/OPV grade: Emphasis on metal ion and halide control, tight batch-to-batch optical specs, and thermal purity—important for reproducible thin-film performance.
• HPLC grade (solvent context) vs. material purity: For solids, purity is often determined by NMR, HPLC/UPLC, GC, and elemental analysis; low-level impurities (halides, Pd, Sn) can affect electronic behavior.

Stabilizers/Additives:

• None indicated for this item. If present in other catalogs (e.g., BHT in monomers), stabilizers can alter oxidative stability and film formation; remove by recrystallization or short-path sublimation when device-grade performance is required.

Recommended verifications before use:

• Confirm identity by 1H/13C NMR and HRMS; assess purity by HPLC/GC.
• For device fabrication, obtain UV–vis and DSC/TGA to benchmark optical gap and thermal transitions.

Always consult the item’s CoA for the definitive specifications of the supplied lot.

Reaction and Applications

Materials and device contexts (general):

• Organic electronics: Building block for small-molecule semiconductors and as a motif in donor units for OPV, OFET, and OLED devices. The thiophene–vinylene–thiophene (TVT) core is known to enhance planarity and charge transport relative to simple bithiophenes.
• Photonics: Conjugated backbones can yield strong absorption and fluorescence in the visible region; useful in sensing and light-harvesting research.

Synthetic reactivity (general guidance):

• Alkene chemistry: The internal vinylene can participate in electrophilic additions, photooxidation, and selective hydrogenation; conjugation tempers reactivity.
• Electrophilic substitution on thiophene rings: Directed bromination/iodination enables downstream cross-coupling to expand oligomer length or introduce solubilizing side chains.
• Cross-coupling: Suzuki–Miyaura, Stille, Kumada, and Negishi couplings are commonly employed on halogenated thiophenes to assemble TVT derivatives.

Practical tips:

• Dry, oxygen-lean conditions improve yields and color stability during synthesis and processing. Employ degassed anhydrous solvents and inert atmosphere when performing metal-catalyzed couplings.
• Purification by recrystallization (aromatics/chlorinated solvents) or vacuum sublimation can deliver device-grade purity.

Note: Manufacturer application details were not provided; above guidance is based on literature precedents for related bithiophene–vinylene systems.

Reaction Conditions

General literature-based conditions for transformations on thiophene–vinylene systems (guidance only; not product specifications):

• Electrophilic halogenation (on thiophene rings):

  • Reagents: NBS/NIS or Br2/I2 under controlled conditions.
  • Solvents: CHCl3, DCM, acetic acid; 0–25 °C to manage regiochemistry.
  • Notes: Protect the vinylene if necessary; monitor to avoid over-bromination.

• Suzuki–Miyaura coupling (on aryl halides derived from the scaffold):

  • Catalyst: Pd(PPh3)4 (1–3 mol%) or Pd2(dba)3 with bulky phosphines.
  • Base: K2CO3, Cs2CO3, or Na2CO3 in H2O/THF or toluene/water biphasic.
  • Temperature: 70–100 °C; 2–16 h.

• Stille coupling (if organostannanes are used):

  • Catalyst: Pd(PPh3)4 or PdCl2(PPh3)2; 0.5–2 mol% Pd.
  • Solvent: Toluene or DMF; 80–110 °C.
  • Note: Minimize tin residues; thorough purification required.

• Hydrogenation of vinylene:

  • Catalyst: Pd/C (5–10 wt%).
  • Solvent: Ethanol, ethyl acetate, or toluene; H2 (1–5 bar); RT–50 °C.
  • Outcome: Saturated bithiophene–ethylene linkage; affects optical gap.

• Thiol–ene addition (to the alkene if accessible):

  • Initiation: UV or radical initiator (AIBN).
  • Solvent: Toluene or bulk; RT–60 °C.

These ranges are typical for related systems; optimize for your substrate and scale.

Safety and Handling

Item-specific hazard data:

• Signal Word: Not specified for this item; refer to SDS.
• H-Statements: Not specified for this item; refer to SDS.
• GHS Classification: Not specified for this item; refer to SDS.
• Pictograms: Not specified for this item; refer to SDS.

General laboratory safety guidance for conjugated heteroaromatic solids (informational; defer to SDS for authoritative instructions):

• Expected hazards: May cause skin/eye irritation and respiratory irritation as nuisance dust; combustible organic solid. Avoid inhalation of particulates and contact with skin/eyes.
• PPE: Use lab coat, safety glasses or goggles, and appropriate chemically resistant gloves (e.g., nitrile). Handle powders in a fume hood to minimize dust exposure.
• Incompatibilities: Strong oxidizing agents may react with sulfur-containing aromatics; avoid strong electrophiles and radical initiators unless intended. Store away from ignition sources.
• First aid overview: If inhaled, move to fresh air; if on skin, wash with soap and water; if in eyes, rinse cautiously with water for several minutes and seek medical attention if irritation persists; if ingested, rinse mouth—do not induce vomiting; seek medical advice. Always follow institutional SOPs.
• Fire-fighting: Use CO2, dry chemical, or foam. Combustion may produce COx, SOx. Firefighters should wear self-contained breathing apparatus.

Storage per Product Data: Store at room temperature. Protect from light and moisture to preserve conjugation and color integrity (general best practice).

Solvent Selection

This conjugated bithiophene–vinylene motif is hydrophobic and typically processed from organic media. Item-specific solubility is not provided; the following is general, literature-based guidance for similar materials.

Preferred solvents for dissolution and film casting (general):

• Aromatics: Toluene, xylenes, chlorobenzene, o-dichlorobenzene — good for higher boiling processing and slow evaporation films.
• Chlorinated solvents: DCM, chloroform, 1,2-dichloroethane — effective for rapid dissolution and spin-coating; consider safety and waste implications.
• Polar aprotics: DMF, NMP, DMSO — useful for annealing studies and where higher polarity improves solvation of planarized structures.

Polarity and miscibility (general):

• Nonpolar-to-moderately polar solute; miscibility governed by solvent π–π interactions and dispersion forces. Poorly soluble in water and light alkanes.

Selection tips:

• Choose higher-boiling aromatics for uniform films and thermal annealing; use lower-boiling chlorinated solvents for quick coating/scouting.
• If aggregation is an issue, modest heating (50–100 °C) and sonication can improve solubility.
• For greener workflows, consider anisole or 2-MeTHF where compatible.

Note: For quantitative solubility and UV-cutoff suitable for optical work, refer to the CoA/SDS and perform a small-scale solubility screen in your intended process solvent.

Storage and Reconstitution

Storage (from Product Data):

• Store at room temperature.

General best practices for conjugated organic solids:

• Keep in a tightly closed container under inert gas (nitrogen/argon) if long-term storage is planned to minimize slow oxidative darkening.
• Protect from direct light and moisture. Store desiccated to avoid clumping and surface oxidation.
• For multiyear retention, consider refrigeration (2–8 °C) in amber glass; allow to warm to ambient in a sealed container before opening to prevent condensation.

Reconstitution/handling:

• Weigh quickly in a low-humidity environment; dissolve in a suitable organic solvent (e.g., chlorobenzene, toluene, chloroform) with gentle warming and sonication as needed.
• Filter solutions through PTFE (0.2 µm) before thin-film processing to remove particulates.
• Prepare fresh solutions for reproducible optical/electronic measurements; prolonged storage of solutions can lead to gradual degradation.

Shipped In: Not specified for this item; refer to CoA/Spec Sheet.

Structure and Identity

Professional summary: This item is a conjugated bithiophene derivative categorized under materials science. The name suggests a bithiophene core connected through an ethenyl (vinylene) linkage at the 2,2′-positions, yielding an extended π-system typical of organic electronic materials.

Item-specific identifiers (from Product Data):

• CAS: 15332-30-6
• Molecular Formula: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular Weight: Not specified for this item; refer to CoA/Spec Sheet.
• SMILES: Not specified for this item; refer to CoA/Spec Sheet.
• InChIKey: Not specified for this item; refer to CoA/Spec Sheet.

Structural features (general/literature-based description):

• Core scaffold: A bithiophene framework (two thiophene rings) connected via the 2,2′-positions.
• Linker: An ethenyl (–CH=CH–) unit bridging the two thiophenes, increasing conjugation relative to 2,2′-bithiophene.
• Functional groups: Aromatic heterocycles (thiophenes) and an internal alkene (vinylene) as part of the conjugated backbone; no heteroatom substituents beyond ring sulfurs.
• Conjugation: Planarizable π-system expected to favor intramolecular charge transfer and lower bandgap versus the non-vinylene analogue.

2D verbal depiction (general): Two five-membered thiophene rings, each bearing a sulfur at position 1, are oriented so their 2-positions are mutually connected through a –CH=CH– unit, generating a linear thiophene–vinylene–thiophene motif (TVT). No stereocenters are present; the central alkene may define E/Z geometry depending on exact substitution pattern (not specified for this item).

Synthetic Utility

As a conjugated bithiophene–vinylene building block, this compound is useful for constructing donor–acceptor oligomers, tuning HOMO/LUMO energies, and modulating planarity in organic electronic materials.

Retrosynthetic/value highlights (general):

• Donor segment: Thiophene units serve as electron-rich donors; the vinylene linkage increases conjugation length and can lower torsional barriers between rings.
• Diversification: Electrophilic halogenation (if positions are available) followed by cross-coupling allows extension to A–D–A motifs, introduction of solubilizing side chains, or anchoring groups for surfaces.
• Post-functionalization: The central alkene can undergo selective hydrogenation (modulating backbone planarity), hydroboration–oxidation (to diols), or thiol–ene click reactions to install side chains.

Integration into materials:

• Small-molecule semiconductors: Incorporation into TVT-centered dyes/push–pull chromophores.
• Polymer chemistry: As a comonomer motif in conjugated polymers, improving charge transport and thermal stability relative to non-vinylene analogues.

Purification and quality:

• Achieve device-grade materials by recrystallization or vacuum sublimation; verify metal content if used downstream after Pd/Ni-catalyzed steps (ICP guidance).

Target Specificity

Not applicable. This product is a small-molecule material and is not an antibody, enzyme, or biological targeting reagent. No antigen/epitope or species reactivity data apply.

Domande frequenti

How should this product be stored?

Store at room temperature.

What are the CAS number, molecular formula and molecular weight?

The CAS Number is 15332-30-6.

What documentation is provided?

Available product documentation, including Certificates of Analysis (COA), Safety Data Sheets (SDS), and specification sheets, is shown in the product document area. Document availability and access follow the current site policy.