Idtt-c16-bis(aldehyde) , CAS No.2241327-13-7

CAS: 2241327-13-7 Cat. No.: I1503601

Storage

Room temperature

Specifiche

Condizioni di conservazione di stoccaggio

Room temperature

Application Protocols

No item-specific tested application protocols are provided for this product. For typical uses in materials synthesis and device fabrication (literature/general):

• Solution preparation for film casting:
  • Dissolve in chlorobenzene or o-dichlorobenzene at 5–20 mg/mL; warm (50–80 C) with stirring until fully dissolved; filter (0.2 µm PTFE) before spin-coating.
• Knoevenagel coupling (general):
  • Combine dialdehyde (1.0 equiv) and active methylene partner (2.1–2.5 equiv) in toluene with catalytic piperidine; fit with Dean–Stark trap; reflux 6–16 h; monitor by TLC/HPLC; purify by column or recrystallization.
• Imine formation (general):
  • Mix with diamine in toluene/EtOH containing 1–10% AcOH; heat 60–100 C; remove water azeotropically or via molecular sieves; isolate by filtration if crystalline.

These are general literature-style procedures; optimize for your system and consult primary references. Always perform risk assessments and small-scale trials before scale-up.

Biological Roles

This product is an organic semiconductor precursor and does not have typical biological roles.

• Not a biomolecule: It is a high–π-conjugation, hydrophobic dialdehyde lacking known physiological function or metabolic pathway relevance.
• Laboratory context: Any interaction with biomolecules (e.g., imine formation with amines) is a chemical reaction rather than a biological role.
• Toxicology/biocompatibility: Not established for biomedical use; no claims of biocompatibility are made. Use strictly for research in materials science.

Conclusion: Biological role discussions are not applicable. Researchers should focus on the synthetic and optoelectronic properties described in other sections.

Buffer Applications

Not typically applicable. Idtt-c16-bis(aldehyde) is a hydrophobic, non-ionic organic semiconductor building block and is not used to prepare aqueous buffers or electrophoresis media. For practical use, see Solvent Selection and Reaction & Applications sections focused on organic-phase processing.

Green Alternatives

Chlorinated solvents are common for conjugated dialdehydes but greener choices can be considered where feasible.

• Potential greener solvents (literature/general):
  • Anisole, 2-methyltetrahydrofuran (2-MeTHF), cyclopentyl methyl ether (CPME), dimethyl carbonate (DMC), propylene carbonate, p-cymene.
  • For high-boiling needs: anisole (bp 154 C) can sometimes substitute chlorobenzene; CPME (bp 106 C) offers hydrophobic ether behavior with low peroxide tendency compared to THF.
• Trade-offs:
  • Solubility may be lower than in o-DCB/chlorobenzene; gentle heating and longer dissolution times may be necessary.
  • Film morphology can shift with different evaporation profiles; process optimization (spin speed, temperature, additive ratios) is required.

Comparison (general trends):

• o-DCB: excellent solubility/film control; poor EHS profile.
• Chlorobenzene: good performance; moderate EHS concerns.
• Anisole: greener; sometimes adequate solubility and similar bp.
• 2-MeTHF/CPME: greener ethers; useful for synthesis and some depositions; lower bp may limit slow-dry morphologies.

Guidance: Start with anisole as a chlorobenzene alternative for deposition trials and CPME/2-MeTHF for synthesis. Validate device metrics and stability after solvent substitution.

Pharmaceutical Uses

Not applicable. This product is not intended as an API or excipient and is not described in pharmacopeias for pharmaceutical formulation.

• Scope of use: Materials science and research applications only (e.g., organic electronics, functional dyes), not for clinical or diagnostic use.
• Regulatory status: No claims are made regarding GMP or compendial compliance for this item.

Refer to the CoA/Spec Sheet for analytical quality details pertinent to research applications.

Physical Properties

• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Purity/Grade: Not specified for this item; refer to CoA/Spec Sheet.
• Melting point (MP): Not specified for this item; refer to CoA/Spec Sheet.
• Boiling point (BP): Not applicable for high-MW conjugated dialdehydes; thermal decomposition may occur before boiling under ambient pressure (general/literature).
• Density: Not specified for this item; refer to CoA/Spec Sheet.
• Refractive index: Not specified for this item; refer to CoA/Spec Sheet.
• Solubility (literature/general for long-alkylated conjugated dialdehydes):
  • Good solubility in chlorinated aromatics (e.g., chlorobenzene, o-dichlorobenzene), chloroform, and hot toluene.
  • Limited solubility in polar protic solvents (water, alcohols) and in alkanes at room temperature.
• LogP, pKa: Not typically defined/used for these non-ionizable, neutral, high-logP materials; values not specified for this item.
• Thermal behavior (literature/general): Conjugated dialdehydes may exhibit distinct glass-transition or crystallization behavior; thermal analysis (TGA/DSC) is recommended to define processing windows for thin-film deposition.
• Optical properties (literature/general): Expect strong π–π* absorption in the visible range attributable to the conjugated core; exact λmax and extinction coefficients must be determined experimentally for the specific batch/system.

Quality and Grades

• Item-specific grade/purity: Not specified for this item; refer to CoA/Spec Sheet.
• Materials science context (general):
  • For optoelectronic materials, key quality dimensions include high chemical purity, narrow isomer content, minimal metal/halide residues, and low water/peroxide content to ensure reproducible device performance.
  • Batch-to-batch consistency is often supported by NMR, HRMS, HPLC/UPLC, and elemental analysis; thin-film applications may also include GIWAXS/AFM correlations.
• Stabilizers/inhibitors: Not specified for this item; refer to CoA/Spec Sheet. If present, stabilizers can influence reactivity of the aldehyde termini (general note).
• Documentation:
  • CoA/Spec Sheet should be consulted for analytical specifications, recommended analytical methods, and acceptance criteria.
• Practical guidance (general):
  • If using in condensation reactions (e.g., Knoevenagel), consider a brief pre-drying under vacuum and/or azeotropic drying to remove trace moisture.
  • For device fabrication, filtration through 0.2 µm PTFE before spin-coating can improve film uniformity by removing particulates.

Reaction and Applications

Applications derive from the conjugated IDTT-type core and the two reactive aldehyde termini.

• Materials science uses (literature/general):
  • Precursor for donor–acceptor chromophores via Knoevenagel condensation with active methylene partners (e.g., malononitrile, 1,3-indandione, barbituric acid) to form push–pull systems for OPV/OSC/photodetectors.
  • Monomeric dialdehyde for constructing small-molecule semiconductors and dyes with tunable bandgaps and absorption onsets.
  • Facilitates end-group engineering to modulate energy levels (HOMO/LUMO) and film morphology.
• Synthetic/transformational reactions:
  • Knoevenagel–Doebner, HWE/Still–Gennari, Wittig olefination to install vinylene linkers.
  • Schiff base formation with diamines to create imine-bridged frameworks or COFs (covalent organic frameworks).
  • Reductive amination to form bis(benzylamine) derivatives; selective reduction (NaBH4/BH3) to alcohols.
• Practical tips (general):
  • Dry, oxygen-free conditions preserve aldehyde integrity and improve yields in base-catalyzed condensations.
  • Use slight excess of active methylene component or employ azeotropic water removal (Dean–Stark) in toluene/xylene to drive equilibrium.
  • For device fabrication, post-deposition thermal or solvent-vapor annealing can optimize molecular packing; verify stability by TGA/DSC and UV–Vis.
• Manufacturer applications: Not specified in the catalog entry; typical uses align with the above literature practices for conjugated dialdehydes.

Reaction Conditions

General literature guidance for dialdehyde transformations; optimize for your system.

• Knoevenagel condensation:
  • Typical solvents: toluene, ethanol/toluene, acetonitrile, or DMF; often conducted under Dean–Stark in toluene/xylene for water removal.
  • Bases/catalysts: piperidine (5–20 mol%), pyridine/acetic acid, ammonium acetate in AcOH; 60–130 C depending on solvent bp.
  • Stoichiometry: 2.0–2.2 equiv active methylene component per dialdehyde; reaction times 2–24 h (literature/general).
• Wittig/Horner–Wadsworth–Emmons (HWE):
  • Solvents: THF, DCM, toluene; temperatures 0–25 C (Wittig) or 0–60 C (HWE) under inert atmosphere.
  • Bases: NaHMDS or n-BuLi for Wittig ylide generation; NaH/DBU/KOtBu for HWE. E-selective Still–Gennari uses electron-withdrawing phosphonates and KHMDS/18-crown-6.
• Imine formation/COF synthesis:
  • Solvent systems: mesitylene/dioxane/AcOH or toluene/EtOH/AcOH; 60–120 C for solvothermal assembly.
  • Catalyst: acetic acid (0.1–6 M) to drive reversible imine exchange toward ordered networks.
• Reduction/oxidation:
  • NaBH4/BH3 or catalytic hydrogenation to alcohols; mild oxidants to acids (e.g., TEMPO/NaClO, Pinnick), as compatible with the conjugated core.

Note: Conditions above are literature/general guidance, not specifications for this item. Verify compatibility with the specific substrate and desired selectivity.

Safety and Handling

• Research use only: For research use only.
• GHS/Signal word/H-statements: Not specified for this item; consult the SDS for authoritative hazard classification.
• General hazard considerations (literature/general for aromatic dialdehydes):
  • Aldehydes can be skin/eye irritants and may cause respiratory irritation; avoid inhalation of dust/particles.
  • Potential sensitization with repeated exposure to some aldehydes.
• PPE: Use lab coat, nitrile gloves, and safety glasses; handle powders in a fume hood or glove box to minimize dust and inhalation.
• Handling practices:
  • Work under dry, inert atmosphere when purity and reactivity must be preserved; aldehydes can hydrate or oxidize over time.
  • Avoid prolonged exposure to light and heat which may promote oxidation or polymerization.
• Incompatibilities (general): Strong oxidizers, strong bases (can induce aldol-type side reactions), primary amines (Schiff base formation), and nucleophiles.
• First-aid overview (general):
  • Skin/eye contact: Rinse with water for at least 15 minutes; remove contaminated clothing; seek medical attention if irritation persists.
  • Inhalation: Move to fresh air; seek medical attention if symptoms occur.
  • Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.
• Waste: Collect organic waste according to institutional and regulatory guidelines; avoid discharge to drains.
• Always defer to the SDS for detailed and binding safety instructions.

Solvent Selection

This compound is a hydrophobic, long-alkylated, conjugated dialdehyde. Solvent choice impacts solubility, reaction kinetics, and film-formation behavior.

• Polarity/miscibility (literature/general):
  • Expected to dissolve well in moderately polar aprotics and chlorinated aromatics: chlorobenzene, o-dichlorobenzene (o-DCB), chloroform, dichloromethane (limited), toluene (hot), THF, and sometimes anisole.
  • Poor solubility in water and aliphatic hydrocarbons at room temperature.
• Processing solvents for thin films (general):
  • o-DCB and chlorobenzene provide higher boiling points, enabling slow drying and improved morphology control.
  • Chloroform affords fast-drying films; may enhance small-grain formation, affecting device parameters.
• Reaction solvents (general):
  • Knoevenagel/condensation: toluene, ethanol/toluene mixtures, acetonitrile, THF, or solvent-free with catalytic base.
  • Wittig/HWE: THF, DCM, toluene, DMF (anhydrous conditions).
• Small comparison (general trends):
  • o-DCB (bp 180 C): high solubility, slow evaporation, good for annealing.
  • Chlorobenzene (bp 132 C): balance of solubility/volatility.
  • THF (bp 66 C): good for synthesis; may be too volatile for uniform large-area films.
• Tip: Filter through 0.2 µm PTFE prior to deposition to remove dust/aggregates; gently heat solutions (50–80 C) to fully dissolve high-MW/conjugated domains.

Storage and Reconstitution

• Storage conditions (item-specific): Room temperature.
• Shipping: Not specified for this item; refer to CoA/Spec Sheet.
• Long-term handling (general best practice for dialdehydes):
  • Store in a tightly sealed amber container under inert atmosphere (nitrogen/argon) with desiccant to minimize moisture and oxygen exposure.
  • Protect from light and excessive heat; avoid repeated heating/cooling cycles that can induce aggregation.
• Reconstitution/dissolution (general):
  • Use dry, oxygen-free solvents for sensitive synthetic steps (THF, toluene, chlorobenzene, o-DCB). Gentle warming (50–80 C) aids dissolution.
  • Filter through 0.2 µm PTFE prior to device deposition to remove particulates.
• Stability notes (general):
  • Aldehyde termini can slowly oxidize or form hydrates/imines with adventitious nucleophiles; minimize exposure to air/amine vapors.
  • For prolonged storage, consider aliquoting to reduce headspace and the number of container openings.

Always consult the product’s CoA/Spec Sheet and SDS for definitive storage and handling instructions.

Structure and Identity

Idtt-c16-bis(aldehyde) is a conjugated organic small molecule/dialdehyde designed for materials science applications, typically as a building block for organic semiconductors and donor–acceptor systems.

• Item-specific identifiers:
  • CAS: 2241327-13-7
  • 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 description, literature-based for IDTT-type dialdehydes):
  • Core: An indacenodithieno[3,2-b]thiophene (IDTT)-like fused polycyclic aromatic framework that imparts planarity and extended π-conjugation (literature/general).
  • Substitution: Long C16 alkyl chains that enhance solubility/processability in organic solvents (literature/general).
  • Functional groups: Two terminal aldehydes (–CHO) positioned in a para/linear fashion relative to the conjugated backbone, enabling bis-condensation chemistry (literature/general).
  • Stereochemistry: Aldehyde-bearing systems are typically achiral as isolated molecules; no stereocenters expected (literature/general).
• 2D structure in words (literature/general): A rigid, flat, polycyclic donor core flanked by two aromatic linkers terminating in aldehyde groups; solubilizing hexadecyl chains append from the core to reduce aggregation and improve film-forming behavior.

Synthetic Utility

The bis(aldehyde) functionality and rigid conjugated core make this compound a versatile synthon for constructing π-extended architectures.

• Functional group leverage (literature/general):
  • Dual –CHO groups enable symmetrical bis-condensations to install electron-withdrawing end groups, tuning ICT strength and bandgap.
  • Compatible with Wittig and HWE reactions to introduce E-alkenyl linkers with controlled stereochemistry.
  • Imine formation with diamines supports crystalline network materials (COFs) and Schiff-base chromophores.
• Retrosynthetic value:
  • Serves as a central donor block; target molecules often disconnect at the vinylene or imine linkers back to this dialdehyde.
  • Offers modularity: selecting different acceptor/active-methylene partners adjusts LUMO level and absorption edge.
• Selectivity/control (general):
  • Use mild bases (piperidine, DBU) and dehydrating conditions to favor clean mono-/bis-condensation as required.
  • Protect from nucleophiles if the aldehyde must be preserved through multistep sequences (e.g., acetal protection, then deprotection with aqueous acid).
• Process considerations:
  • High hydrophobicity and C16 chains aid solubility in high-boiling organic solvents, facilitating scale-up and film casting from concentrated solutions.

Target Specificity

Not applicable. This product is a small-molecule building block, not a biological targeting reagent, antibody, or probe with defined antigen/epitope specificity.

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 2241327-13-7.

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.