IDT-C2C6-Dibromobis

Cat. No.: I1503593

Storage

Room temperature

Specifiche

Condizioni di conservazione di stoccaggio

Room temperature

Application Protocols

Item-specific tested protocols are not provided for this product. For research use only. General starting points (literature/general) are provided for convenience and must be optimized for the actual structure.

• Small-scale polymerization screen (Suzuki example):

  • Charge dry flask with IDT-type dibromide (1.00 equiv), bis(pinacol) boronate comonomer (0.98–1.02 equiv), Pd(PPh3)4 (1 mol% Pd), K2CO3 (3.0 equiv, 2 M aq.), anisole (0.2–0.5 M w.r.t. repeat unit), water (10–20% v/v). Degas, heat to 95 C for 18 h under N2. End-cap with phenylboronic acid then bromobenzene, precipitate polymer into methanol, filter, and Soxhlet extract (MeOH, acetone, hexanes, then chloroform).

• Film preparation (general):

  • Dissolve polymer in chlorobenzene or anisole (5–15 mg/mL) at 80–120 C with stirring; filter (0.45 µm PTFE) hot; spin-coat or blade-coat in N2 glovebox. Anneal as required.

These are general templates. Validate stoichiometry, solubility, and thermal limits against the item’s CoA/Spec Sheet and SDS.

Biological Roles

This material is supplied for materials science research and is not intended for biological applications.

General note (literature/general):

• Aromatic dibromide monomers like those used for IDT-based conjugated polymers do not have intrinsic biological roles or metabolic functions. They are engineered for optoelectronic properties (e.g., charge transport, absorption) in solid-state devices.
• Any interaction with biological systems has not been characterized here and should not be inferred. If biocompatibility or bioelectronics interfaces are of interest, separate studies with the final polymeric material are required.

For all biological or biomedical inquiries, no claims are made; research use only.

Buffer Applications

Not typically applicable.

Rationale: As a hydrophobic aromatic monomer for materials science, this product is not used to prepare aqueous buffers or biological buffer systems. If your workflow involves aqueous processing (e.g., nanoparticle dispersions of the resulting polymer), buffer selection would pertain to the formulated dispersion, not to this monomer. Refer instead to Solvent Selection and Reaction & Applications for relevant guidance.

Green Alternatives

While item-specific composition is not provided, greener strategies can be adopted for typical cross-coupling/polymerization of aryl dibromides (literature/general). Tradeoffs must be evaluated experimentally.

Greener choices overview (general):

• Solvents:
  • Replace chlorinated aromatics with anisole, 2-methyltetrahydrofuran (2-MeTHF), cyclopentyl methyl ether (CPME), or propylene carbonate when solubility allows.
  • For aqueous Suzuki couplings, use toluene/water or anisole/water biphasic systems with phase-transfer bases.
• Catalysts/ligands:
  • Employ low-Pd loading systems (ppm-level) with robust ligands (e.g., Buchwald-type) or heterogeneous Pd/C under controlled conditions to reduce metal waste.
  • Nickel catalysis can be viable for activated aryl bromides, potentially lowering cost and improving sustainability.
• Processes:
  • Direct (C–H) arylation polymerization (DArP) avoids prefunctionalization, eliminating boron/tin waste streams.
  • Flow chemistry with improved heat/mass transfer can reduce solvent volumes and reaction times.

Concise comparison (general):

• o-DCB vs anisole: o-DCB offers higher solubility and thermal window; anisole provides lower toxicity and improved EHS profile but may need higher temperatures or cosolvents.
• Stille vs Suzuki: Stille is tolerant but generates toxic tin waste; Suzuki uses benign boron byproducts and can run in water-containing media.

Recommendation: Start with anisole or anisole/propylene carbonate and Suzuki catalysis; if solubility limits performance, escalate to o-DCB or TCB with appropriate controls.

Pharmaceutical Uses

Not applicable to this product’s intended use.

Context: This item is a research-grade materials science monomer for organic electronics and related advanced materials. It is not an excipient and has no pharmacopeial status provided in the Product Data. No claims are made for pharmaceutical formulation or manufacturing.

For any regulatory or GMP-related considerations in materials-enabled devices, request full specifications and supporting documentation separately.

Physical Properties

Item-specific physical properties are not specified for this item; refer to CoA/Spec Sheet.

• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Melting point: Not specified for this item; refer to CoA/Spec Sheet.
• Boiling point: Not applicable/unknown for high-MW aromatic solids; specific value not specified for this item; refer to CoA/Spec Sheet.
• Density: Not specified for this item; refer to CoA/Spec Sheet.
• Solubility: Not specified for this item; refer to CoA/Spec Sheet.
• LogP, pKa, refractive index: Not specified for this item; refer to CoA/Spec Sheet.

Literature/general expectations for IDT-type dibromo monomers (not item-specific):

• Physical state: typically dark-colored crystalline solids or powders.
• Solubility: engineered side chains (e.g., C2/C6) are used to increase solubility in chlorinated aromatics (chlorobenzene, o-dichlorobenzene), anisole, or high-boiling ethers; solubility decreases in alkanes and alcohols.
• Thermal behavior: rigid fused aromatics often exhibit sharp melting or decomposition on DSC/TGA; processing windows commonly extend >200 C, but exact onset temperatures are structure-dependent.

Note: For quantitative values that govern processing (e.g., solubility at set temperatures, glass transition), consult the item’s CoA/Spec Sheet or request a technical data package. Do not substitute literature values for specifications in regulated workflows.

Quality and Grades

Item-specific grade/purity information is not specified for this item; refer to CoA/Spec Sheet.

General guidance (literature/general):

• Polymerization monomer quality: For Pd-catalyzed cross-coupling polymerizations, low levels of metal impurities, water, and residual halogenated solvents are desirable to ensure high molecular weights and narrow dispersity.
• Purity considerations: Trace protodebrominated species, mono-brominated impurities, and residual catalyst ligands from synthesis can act as chain stoppers. High-performance purification (e.g., recrystallization, preparative chromatography, or sublimation when feasible) is often employed.
• Documentation: Request CoA with HPLC/GC purity, NMR identity, halogen content verification, and residual solvent/metal screening when needed for reproducible device-grade materials.

What the grade means (context):

• “Electronic grade” or “OPV/OLED grade” (if applicable on a spec sheet) typically indicates tighter controls on insolubles/particulates and UV-vis baseline for thin-film optics. In the absence of an item-specific designation, treat this as a research-grade material and validate in your process.

Recommendation: For sensitive polymerizations, pre-dry the monomer and solvents, and consider a small test polymerization to benchmark Mn/Mw and defect density before scale-up.

Reaction and Applications

Manufacturer Applications: Not specified in Product Data.

Expanded context (literature/general for IDT-type “Dibromobis” monomers):

• Role: bifunctional aryl dibromide monomer designed for step-growth polymerizations to yield conjugated donor polymers for organic electronics (OPV, OLED, OFET). The dibromo motif enables cross-coupling with complementary di-boronates, di-stannanes, or C–H partners.
• Key reaction families:
  • Suzuki–Miyaura polymerization with bis(pinacol boronate) or boronic acid comonomers; broad functional group tolerance, water-assisted bases.
  • Stille polymerization with distannylated acceptors/donors; robust toward base-sensitive motifs, but involves organostannanes.
  • Direct (C–H) arylation polymerization (DArP/DHAP) using Pd catalysts and carboxylate bases; potential to avoid prefunctionalization and tin waste.
• Device relevance: resultant polymers often exhibit high hole mobilities and favorable film morphology due to the planar IDT core and tuned side chains; properties depend on comonomer selection and processing.
• Practical notes:
  • Drying: pre-dry monomer under vacuum at moderate temperature if thermally safe; water can inhibit coupling.
  • Catalyst/ligand selection and base choice markedly affect molecular weight and dispersity; screen conditions at millimole scale.
  • End-group control: slight stoichiometric offsets or addition of monofunctional capping agents can tune Mn and suppress defects.

All applications are for research use only. Verify monomer identity and purity with NMR and elemental/halogen analysis prior to polymerizations.

Reaction Conditions

Item-specific recommended conditions are not specified for this item; refer to CoA/Spec Sheet. The following are literature/general guidelines for aryl dibromide IDT-type monomers in step-growth polymerizations. Adjust based on actual structure and solubility.

• Suzuki–Miyaura polymerization (literature/general):

  • Catalyst: Pd(PPh3)4 (0.5–3 mol% Pd) or Pd2(dba)3/XPhos-type ligands.
  • Base: K2CO3 or Cs2CO3 (2–3 equiv), often with aqueous component; optional PivOH as additive.
  • Solvent: toluene/water, anisole/water, or o-DCB; 80–110 C; 12–48 h under N2/Ar.
  • End-capping: phenylboronic acid and bromobenzene sequentially to quench chain ends.

• Stille polymerization (literature/general):

  • Catalyst: Pd(PPh3)4 or Pd2(dba)3 with tri(o-tolyl)phosphine; 0.5–2 mol% Pd.
  • Solvent: chlorobenzene, o-DCB, or anisole; 90–120 C; 12–48 h.
  • Note: rigorously exclude oxygen; handle organostannanes with appropriate PPE and waste protocols.

• Direct (C–H) arylation polymerization (literature/general):

  • Catalyst/base: Pd(OAc)2 (0.5–2 mol% Pd), KOAc/K2CO3, with PivOH; 90–120 C.
  • Solvent: dimethylacetamide (DMAc), NMP, anisole, or propylene carbonate; inert atmosphere.

Process controls:

• Monitor monomer conversion by aliquot GPC (precipitate polymer) or by disappearance of Ar–Br signals in 1H/13C NMR of low-Mn fractions.
• Viscosity management: incremental solvent addition or temperature ramps can prevent gelation during high-MW growth.

Safety and Handling

Item-specific hazard and GHS information are not specified for this item; refer to SDS.

• Signal word: Not specified for this item; refer to SDS.
• Hazard statements (H-codes): Not specified for this item; refer to SDS.
• GHS classification/pictograms: Not specified for this item; refer to SDS.

General handling guidance for aromatic dihalide monomers (literature/general):

• Avoid dust generation; use local exhaust ventilation and a particulate respirator if dusting is possible.
• Wear appropriate PPE: lab coat, safety glasses, and chemically resistant gloves (e.g., nitrile). For prolonged handling or weighing, consider double-gloving.
• Incompatibilities: strong nucleophiles and organometallic reagents can react; store separately from strong bases/acids and oxidizers. Keep away from ignition sources when using high-boiling organic solvents.
• Thermal processing: when used in high-temperature polymerizations, employ closed systems or reflux condensers and ensure adequate headspace venting.
• First aid (overview): eye/skin contact—rinse with water for at least 15 minutes; inhalation—move to fresh air; ingestion—rinse mouth. Seek medical attention per SDS.
• Waste: halogenated aromatic residues and coupling byproducts should be collected as hazardous organic waste in compliance with institutional and local regulations.

Always consult the product-specific SDS before use. Research use only.

Solvent Selection

Item-specific solvent compatibility and solubility data are not specified for this item; refer to CoA/Spec Sheet.

General solvent strategy for IDT-type dibromo monomers (literature/general):

• Polarity class: weakly to moderately polar, aromatic; favors aromatic or chlorinated aromatic solvents.
• Typical solvents: chlorobenzene (CB), o-dichlorobenzene (o-DCB), 1,2,4-trichlorobenzene (TCB), anisole, mesitylene; for processing or polymerizations at elevated temperatures, high-boiling choices (o-DCB, TCB) are common.
• Miscibility: generally insoluble in water; miscible with many organic solvents depending on side chains; solubility often increases with temperature.

Selection tips:

• For thin-film deposition: choose a solvent that dissolves both monomer and resulting polymer at the working temperature to avoid premature precipitation; CB or anisole often balance volatility and film uniformity.
• For Suzuki/Stille polymerizations: mixed solvent systems (e.g., toluene/water, toluene/DMF, anisole/propylene carbonate) can improve kinetics and heat transfer.
• For purification: hot filtration in anisole or chlorinated aromatics can remove particulates; antisolvents (methanol/hexanes) may precipitate target polymers.

Comparison (general):

• o-DCB: higher solubility window, higher bp; slower drying, good for high-MW growth.
• Anisole: greener profile, lower toxicity; may require higher temperatures or cosolvents to dissolve rigid monomers.

Validate solvent choice with a small-scale solubility screen at target temperature.

Storage and Reconstitution

• Storage conditions (from Product Data): Room temperature.
• Shipped in: Not specified for this item; refer to CoA/Spec Sheet.
• Reconstitution: Not applicable; this is a solid organic monomer rather than a biologic lyophile. If preparing solutions, use anhydrous, oxygen-free solvents appropriate to your application.

General practices (literature/general):

• Store tightly sealed in a dry environment, protected from prolonged light exposure. For best reproducibility in cross-couplings, consider storing under inert gas if the container will be opened frequently.
• Before use, optionally dry under vacuum at a temperature safely below any melting/decomposition onset (consult CoA/DSC/TGA if available).
• Solution stability: solutions in high-boiling aromatics can slowly oxidize; prepare fresh or store under inert atmosphere at ambient temperature away from light.
• Freeze–thaw: not applicable to solids. If solution stocks are prepared, aliquot to minimize air/moisture ingress.

Research use only. Consult the SDS for detailed handling and storage incompatibilities.

Structure and Identity

Item-specific structural identifiers are not specified for this item; refer to CoA/Spec Sheet.

• Product name (catalog): IDT-C2C6-Dibromobis (materials science category)
• SKU: I1503593
• CAS: Not specified for this item; refer to CoA/Spec Sheet.
• 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.

General chemistry context (literature/general):

• The designation “IDT-C2C6” is commonly used in the organic electronics community to denote indacenodithiophene (IDT) cores bearing mixed short/branched alkyl side chains (e.g., ethyl/hexyl patterns) to tune solubility and packing. The suffix “Dibromobis” typically denotes a di-brominated, bifunctional monomer suitable for Pd-catalyzed cross-coupling polymerizations.
• Structural features likely include: a fused polycyclic donor core (IDT) with two aryl bromide leaving groups positioned for step-growth polymerization. Exact regiochemistry and side-chain identity must be confirmed on the CoA/Spec Sheet.

2D structure description (general):

• A rigid, planarized polycyclic central scaffold with two brominated aryl termini (para- or bay-positions); solubilizing alkyl chains extend from the core to enhance solution processability. Stereochemistry is typically not a focus unless chiral side chains are employed.

Synthetic Utility

General synthetic utility for aryl “Dibromobis” IDT-type monomers (literature/general):

• Functional group handle: two aryl bromides positioned for Pd- or Ni-catalyzed cross-coupling serve as leaving groups, enabling step-growth polymerization with di-boronates, di-stannanes, or via C–H activation.
• Key transformations:
  • Suzuki–Miyaura coupling/polymerization with bis(pinacol) boronates to build donor–acceptor backbones; water-tolerant, greener byproducts.
  • Stille coupling/polymerization with distannyl partners; robust for challenging substrates but produces tin waste.
  • Direct arylation polymerization (DArP/DHAP) using carboxylate bases (e.g., KOAc) and Pd catalysts, avoiding prefunctionalization.
  • Post-functionalization: remaining positions on the core (if any) can be leveraged for side-chain tuning via Friedel–Crafts alkylation or halogenation (structure-dependent; verify compatibility).
• Retrosynthetic value: The dibromo monomer is a convergent node; pairing with a complementary di-electrophile or di-nucleophile enables systematic library generation of copolymers to tune bandgap, planarity, and solubility.
• Practical insights:
  • Stoichiometry control (±0.5–1.0%) is critical to achieve high Mn and low end-group defects.
  • Purity of base and dryness of solvent/catalyst stocks profoundly influence polymer growth and defect density.

These are general guidelines; confirm reactivity and regiochemistry with the item’s structure from the CoA/Spec Sheet.

Target Specificity

Not applicable. This product is not a biological targeting reagent (e.g., antibody, ligand, probe). No antigen/epitope specificity or species reactivity is associated with this materials science monomer.