ITIC - ≥98% , CAS No.1664293-06-4

CAS: 1664293-06-4 Cat. No.: I432187 Formula: C₉₄H₈₂N₄O₂S₄ Molecular Weight: 1427.94

GRADE & PURITY ≥98%

Synonyms

2,2′-[[6,6,12,12-Tetrakis(4-hexylphenyl)-6,12-dihydrodithieno[2,3-d:2′,3′-d′]-s-indaceno[1,2-b:5,6-b′]dithiophene-2,8-diyl]bis[methylidyne(3-oxo-1H-indene-2,1(3H)-diylidene)]]bis[propanedinitrile]

Storage

Protected from light,Room temperature

Shipped In

Normal

Overview

ITIC, non-fullerene acceptor, is an indacenodithienothiophene-based postfullerene electron acceptor, crystallizes in a profoundly different way as compared to fullerenes. ITIC has a superior thermal stability and undergoes a glass-crystal transition considerably below its high Tg of 180 °C.

Application：

ITIC is a specific non-fullerene acceptor (NFA) molecule used in Organic Photovoltaics(OPVs). ITIC offers potential advantages over traditional fullerene-based acceptors such as include higher Voc (open-circuit voltage), improved stability and broader absorption properties.

Specifications

Synonyms

2,2′-[[6,6,12,12-Tetrakis(4-hexylphenyl)-6,12-dihydrodithieno[2,3-d:2′,3′-d′]-s-indaceno[1,2-b:5,6-b′]dithiophene-2,8-diyl]bis[methylidyne(3-oxo-1H-indene-2,1(3H)-diylidene)]]bis[propanedinitrile]

Specifications & Purity

≥98%

Storage

Protected from light,Room temperature

Shipped In

Normal

Purity

≥98%

Names and Identifiers

Pubchem Sid

504773022

Pubchem Sid Url

https://pubchem.ncbi.nlm.nih.gov/substance/504773022

Canonical Smiles

CCCCCCC1=CC=C(C=C1)C2(C3=CC4=C(C=C3C5=C2C6=C(S5)C=C(S6)C=C7C(=C(C#N)C#N)C8=CC=CC=C8C7=O)C(C9=C4SC1=C9SC(=C1)C=C1C(=C(C#N)C#N)C2=CC=CC=C2C1=O)(C1=CC=C(C=C1)CCCCCC)C1=CC=C(C=C1)CCCCCC)C1=CC=C(C=C1)CCCCCC

IUPAC Name

2-[2-[[20-[(Z)-[1-(dicyanomethylidene)-3-oxoinden-2-ylidene]methyl]-12,12,24,24-tetrakis(4-hexylphenyl)-5,9,17,21-tetrathiaheptacyclo[13.9.0.03,13.04,11.06,10.016,23.018,22]tetracosa-1(15),2,4(11),6(10),7,13,16(23),18(22),19-nonaen-8-yl]methylidene]-3-oxoinden-1-ylidene]propanedinitrile

InChIKey

HQOWCDPFDSRYRO-CDKVKFQUSA-N

INCHI

1S/C94H82N4O2S4/c1-5-9-13-17-25-59-33-41-65(42-34-59)93(66-43-35-60(36-44-66)26-18-14-10-6-2)79-53-76-80(54-75(79)89-85(93)91-81(103-89)51-69(101-91)49-77-83(63(55-95)56-96)71-29-21-23-31-73(71)87(77)99)94(67-45-37-61(38-46-67)27-19-15-11-7-3,68-47-39-62(40-48-68)28-20-16-12-8-4)86-90(76)104-82-52-70(102-92(82)86)50-78-84(64(57-97)58-98)72-30-22-24-32-74(72)88(78)100/h21-24,29-54H,5-20,25-28H2,1-4H3/b77-49-,78-50?

Molecular Weight

1427.94

Reaxy-Rn

27925865

Reaxys-RN_link_address

https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=27925865&ln=

Chemical and Physical Properties

• Sensitivity: Light sensitive；Heat sensitive

Application Protocols

Item-specific, validated application protocols are not provided for this SKU. Refer to the literature examples below as general starting points (non-spec) and optimize for your system.

General OPV fabrication workflow (example)

• Substrates: ITO-coated glass cleaned by sequential sonication (detergent → water → acetone → IPA), dried, and O2 plasma-treated.
• Interlayers: spin-coat ZnO (sol–gel or nanoparticle) for inverted stacks or PEDOT:PSS for conventional stacks; bake per supplier guidance.
• Active layer: prepare donor:ITIC solution in chlorobenzene or o-DCB (e.g., 1:1 w/w, 10–20 mg/mL total solids) with optional 0.5–2% DIO. Warm, filter, and spin-coat to 80–120 nm thickness.
• Post-treatment: thermal anneal (e.g., 100–120 °C, 10 min) or solvent vapor anneal as needed.
• Electrodes: deposit MoOx/Ag (conventional) or PEIE/Al (inverted) as per device design.
• Characterization: measure UV–vis, J–V under AM 1.5G, EQE, AFM/GIWAXS for morphology.

Note

• Parameters are donor-, solvent-, and architecture-dependent. Perform design of experiments (DoE) for rapid optimization.

Biological Roles

Not typically applicable.

General information

• ITIC is a synthetic, conjugated small molecule designed for electronic/optoelectronic applications. It has no known natural biological role, metabolic pathway, or enzymatic function.
• Biological testing is not the intended use; any interaction with biological systems (e.g., cytotoxicity, biodegradability) would be outside the scope of this materials-science product and should be independently assessed under appropriate biosafety and regulatory frameworks if contemplated.

Note

• For research use only. Not for human or animal diagnostic or therapeutic applications.

Buffer Applications

Not applicable.

Rationale

• ITIC is insoluble in aqueous media and is not used to prepare pH buffers or biological buffer systems. For this product, see Solvent Selection, Reaction & Applications, and Synthetic Utility for relevant usage guidance.

Green Alternatives

Goal: reduce reliance on chlorinated, high-toxicity solvents without sacrificing film quality.

General guidance (literature/non-spec)

• Greener solvent candidates for ITIC processing include:
  • o-Xylene, mesitylene: non-chlorinated aromatics with suitable solubility at elevated temperature; slower drying than chloroform, aiding morphology control.
  • Anisole, ethyl phenylacetate: higher-boiling, lower-toxicity ether/ester solvents; may require co-solvents or substrate heating.
  • 2-Methyltetrahydrofuran (2-MeTHF), cyclopentyl methyl ether (CPME): greener ethers; solubility of ITIC can be limited, but blends with aromatics may work.
  • Terpineol or limonene-based solvent systems: bio-derived options explored for scalable coating; typically need elevated temperatures and longer drying windows.

Compact comparison (non-spec)

• Chloroform/chlorobenzene: excellent solubility/film uniformity; environmental/health concerns; widely used in labs.
• o-Xylene/mesitylene: reduced toxicity; require thermal assistance; may shift morphology and require additive re-optimization.
• Anisole/EPA: greener profile; viscosity/evaporation differ—affects coating windows.

Best practices

• Start with a CB:o-xylene or anisole:o-DCB blend to balance solubility and drying kinetics.
• Increase substrate and solution temperature (50–90 °C) for non-chlorinated systems; maintain inert atmosphere to minimize oxidative/photoinduced changes.
• Re-optimize additive type/level and annealing when changing solvent to maintain device performance.

Pharmaceutical Uses

Not applicable to this product.

Context

• ITIC is an organic semiconductor intended for materials research (e.g., OPV/OPD). It is not an excipient, API, or processing aid in pharmaceutical manufacturing, and it is not covered by pharmacopeial monographs.

Compliance note

• For research use only. Not for use in humans or clinical settings.

Physical Properties

Item-specific (from Product Data)

• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular Weight: Not specified for this item; refer to CoA/Spec Sheet.
• Other specifications (mp/bp/density/UV cutoff/logP, etc.): Not specified for this item; refer to CoA/Spec Sheet.

Literature/General (non-spec) properties for archetypal ITIC-type NFAs

• Physical state: dark solid (typically dark green/black powders for conjugated acceptors), strongly absorbing in the visible–NIR due to an extended π-system.
• Solubility profile: good solubility in chlorinated aromatics (chlorobenzene, o-dichlorobenzene) and some chlorinated solvents (chloroform), often soluble in high-boiling aromatic ethers (e.g., anisole) with thermal or additive assistance; effectively insoluble in water and lower alcohols (MeOH, EtOH). Film formation from CB, CF, o-DCB, or mixed solvent/additive systems (e.g., 0.5–3% 1,8-diiodooctane) is common in OPV processing.
• Thermal behavior: high thermal stability typical of ladder-type small-molecule acceptors; glass transition and melting features depend on exact substitution and polymorph; decomposition generally well above typical device processing temperatures (<200 °C).
• Optoelectronic attributes: strong charge-transfer absorption band in the red; frontier orbital levels (HOMO/LUMO) and optical bandgap are formulation- and polymorph-dependent; consult primary literature for specific values for the particular ITIC grade/variant.

Important

• Do not use the above as product specifications. For exact values relevant to SKU I432187, please consult the CoA/Spec Sheet.

Quality and Grades

Item-specific (from Product Data)

• Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.

How to interpret quality for ITIC-type OPV materials (general guidance)

• Purity dimensions: beyond standard chemical purity, device-grade small-molecule semiconductors benefit from tight control of isomeric purity, end-group integrity (e.g., intact dicyanomethylene-indanone), and absence of low-MW residuals that can plasticize films.
• Residual metals: catalytic metals (e.g., Pd, Sn) from cross-coupling routes can impair electronic properties and must be minimized (often assessed by ICP-MS). Residual halides can also affect stability.
• Particle size/dispersion: for solution processing, consistent particle size and ease of dissolution reduce filtration losses and pinhole formation.
• Optical quality: low baseline UV–vis absorbance in the processing solvent and absence of scattering particulates are critical for reproducible film formation.
• Documentation: request CoA/Spec Sheet for analytical methods (HPLC/UPLC, NMR, HRMS, elemental analysis, ICP-MS) and any application testing (e.g., film morphology by AFM/GIWAXS) if available.

Stabilizers/additives

• Stabilizers are generally not used for OPV small molecules; if present, they will be declared on the CoA/Spec Sheet. Effects on film morphology and device metrics should be considered if any additives are included.

Reaction and Applications

Item-specific (from Product Data)

• Category: Materials Science; For research use only.

Applications (literature/general; non-spec)

• Organic photovoltaics (OPV): ITIC is a benchmark non-fullerene acceptor employed in bulk heterojunction (BHJ) active layers with donor polymers. It enables broad absorption and favorable energetics for efficient exciton dissociation and charge transport.
• Organic photodetectors (OPD) and NIR sensing: broad, strong CT absorption and low-dark-current potential make ITIC-based blends candidates for solution-processed photodetectors.
• Thin-film electronics: as an electron-transporting acceptor in blends or neat films; occasionally explored in OFETs and perovskite interlayers.

Practical notes for device fabrication

• Solution prep: dry, oxygen-free solvents improve reproducibility; gentle heating (50–100 °C) with stirring or brief sonication aids dissolution.
• Film formation: control evaporation rate (substrate temperature, solvent boiling point, ambient), and consider additives to tune nanoscale phase separation with the donor.
• Post-treatments: thermal annealing (e.g., 80–140 °C) and/or solvent vapor annealing can optimize crystallinity and domain purity; conditions are donor-dependent.
• Substrate handling: use UV-ozone or oxygen plasma to clean ITO; optimize interlayers (e.g., ZnO, PFN-Br on cathode side; MoOx/PEDOT:PSS on anode side) for energetics and wetting.

Note

• Device performance depends sensitively on donor selection, solvent system, film thickness, and annealing; optimize empirically for your stack.

Reaction Conditions

Two contexts are relevant: solution processing for devices and synthetic formation of the A–D–A molecule. Values below are literature-style general guidance (non-spec) and must be optimized per system.

A. Film casting and device fabrication

• Solutions: 5–20 mg/mL total solids in chlorobenzene or o-DCB; 0.5–3 vol% high-boiling additive as needed. Warm (50–100 °C) and filter (0.20 μm PTFE) before coating.
• Coating: spin at 1000–3000 rpm for 30–90 s (lab-scale) or blade/slot-die with 60–120 °C substrate temperature (scale-up). Control ambient (<30% RH) and minimize UV exposure.
• Post-treatment: thermal anneal 5–20 min at 80–140 °C; solvent vapor annealing (e.g., CB, CF, CN vapors) can further tune morphology. Optimize per donor and stack.

B. Key synthetic steps

• Knoevenagel condensation: dialdehyde core + IC in toluene, chlorobenzene, or acetonitrile with catalytic piperidine or ammonium acetate; reflux or 80–120 °C; Dean–Stark for water removal when applicable; hours to overnight. Monitor by TLC/UV–vis.
• Cross-coupling to build core: Pd-catalyzed Suzuki (XPhos/Pd2(dba)3) or Stille (Pd(PPh3)4) in toluene/DMF or xylene, 90–120 °C, 6–24 h under N2; aqueous workup, followed by Soxhlet extraction.

Notes

• Exact conditions depend on the chosen ITIC variant, solvent system, and donor partner. Always confirm compatibility with your interlayers and electrodes.

Safety and Handling

Item-specific (from Product Data)

• Storage Conditions: Protect from light; room temperature. Ship at ambient conditions (Normal).
• GHS Classification / Signal Word / Pictograms / H-Statements: Not specified for this item; refer to SDS.

General laboratory safety guidance (non-spec; defer to SDS)

• Likely hazards: organic, polycyclic aromatic/heteroaromatic solids can cause mechanical irritation to eyes/skin and respiratory tract as dusts; combustion may produce CO/CO2/NOx/SOx.
• PPE: lab coat, safety glasses or goggles, appropriate gloves (e.g., nitrile) when handling solid or solutions. Avoid generating dust/aerosols. Work under local exhaust when weighing.
• Light sensitivity: given the photoactive nature, minimize exposure to intense light during solution preparation and film casting to avoid unintended photochemical changes; amber containers recommended.
• Incompatibilities: strong oxidizers, strong acids/bases under heating; avoid halogenating agents. Ensure solvents used for processing are compatible and dry if required for device fabrication.
• First aid (overview):
  • Inhalation: move to fresh air; seek medical attention if symptoms persist.
  • Skin contact: wash with soap and water; remove contaminated clothing.
  • Eye contact: rinse cautiously with water for several minutes; remove contact lenses if present and easy; seek medical advice if irritation continues.
  • Ingestion: rinse mouth; seek medical attention.
• Spills: avoid dust; collect mechanically or damp-wipe; dispose according to local regulations.

Always consult the product-specific SDS for authoritative hazard and response information before use.

Solvent Selection

Context: ITIC-type NFAs are processed from solution to form thin films for OPV/OPD devices. Solvent choice controls solubility, drying kinetics, phase separation with donor polymers, and final morphology.

Literature/General guidance (non-spec)

• Polarity/miscibility: best solubility in moderately polar, aromatic or chlorinated aromatic solvents (chlorobenzene, o-dichlorobenzene). Miscible with common chlorinated solvents (chloroform, dichloromethane) but volatility may be too high for uniform films without additives.
• High-boiling options: o-DCB, chlorobenzene, 1-chloronaphthalene (as cosolvent/additive) for slow drying and enhanced crystallinity. Anisole or mesitylene can be used in greener formulations with thermal assistance.
• Additives: small % of high-boiling additives (e.g., 1,8-diiodooctane, diphenyl ether, 1-phenylnaphthalene) often tunes donor–acceptor phase separation; optimize empirically.
• Donor polymer compatibility: solvents must dissolve both donor (e.g., PM6, PBDB-T, PTB7-Th) and ITIC; binary/ternary solvent systems are common for balanced solubility.
• Processing techniques: spin-coating, blade/slot-die coating, and meniscus-guided coating benefit from solvent systems that maintain a stable wet film and controlled evaporation rate.

Selection tips

• Start with chlorobenzene or o-DCB for lab-scale spin-coating; screen co-solvents (1–10%) to tune morphology.
• For scalable coating, evaluate o-xylene/anisole blends at elevated substrate temperature to reduce chlorinated solvent use, checking for solubility limits.
• Always filter hot solutions (0.20–0.45 μm PTFE) immediately before coating to remove particulates and pre-aggregates.

Storage and Reconstitution

Item-specific (from Product Data)

• Storage: Protect from light. Store at room temperature. Ship at ambient conditions (Normal).

General handling and solution preparation (non-spec)

• Container: store in amber glass with PTFE-lined cap to minimize light and oxygen exposure. Purge headspace with inert gas (N2/Ar) after each use for best shelf life.
• Solid handling: minimize repeated heating/cooling cycles; keep desiccated to avoid moisture uptake by packaging and to maintain consistent weighing.
• Stock solutions: prepare in dry, oxygen-free solvent (e.g., chlorobenzene, o-DCB, chloroform). Typical concentrations for coating are 5–20 mg/mL; dissolve with mild heating (50–100 °C) and stirring. Filter solutions (0.20 μm PTFE) immediately before coating.
• Stability: solutions are light-sensitive; store in amber vials at room temperature or 4 °C, and use within days for best reproducibility. Discard if precipitation, color change, or significant baseline absorbance drift is observed.
• Freeze–thaw: not applicable to the solid; avoid freezing/thawing solutions repeatedly as precipitation and aggregation may occur.

Documentation

• For product-specific shelf life, impurity profile, and any stabilizers, consult the CoA/Spec Sheet and SDS.

Structure and Identity

Item-specific (from Product Data)

• Product Name: ITIC (SKU: I432187)
• CAS: 1664293-06-4
• PubChem CID: 126843541
• InChIKey: 128471 (as provided)
• SMILES: 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.

Literature/General description (non-spec)

• Compound class: non-fullerene acceptor (NFA) for organic photovoltaics; small-molecule, A–D–A architecture.
• Canonical name used in literature: ITIC typically denotes an indacenodithienothiophene (IDTT)-based donor core flanked by two 1,1-dicyanomethylene-3-indanone (IC/INCN) electron-withdrawing end groups.
• Key structural features: highly conjugated, rigid, near-planar polycyclic core; four aryl/alkylphenyl substituents on the central donor framework to tune solubility and intermolecular packing; terminal dicyanomethylene-indanone moieties providing strong acceptor strength.
• Functional groups: multiple aromatic rings (thiophene-fused), two carbonyls (indanone), four nitriles (dicyanomethylene groups), thienyl sulfur heteroatoms; no formal stereocenters (overall achiral).
• 2D description: a central indacenodithienothiophene ladder-type core bearing two opposite vinylic linkers that connect to cyano-rich indanone caps; lateral 4-hexylphenyl-like substituents installed on the core periphery enhance solubility in aromatic solvents.

Notes

• Structural identifiers and exact substituent patterns can vary across ITIC analogues; the above describes the archetypal ITIC reported in OPV literature and is provided for contextual understanding only.

Synthetic Utility

Although ITIC is typically a final functional material rather than a reagent, understanding its retrosynthesis aids customization and derivatives development.

Literature/general synthesis outline (non-spec)

• Core construction: the indacenodithienothiophene (IDTT) core is assembled via cross-coupling (e.g., Stille/Suzuki) of halogenated thiophene and aryl units, followed by intramolecular cyclization/annulation to form the ladder-type framework. Regioselective installation of aryl/alkylphenyl substituents tunes solubility and packing.
• Formylation: the core’s 2,8-positions are converted to dialdehyde via lithiation/formylation or Vilsmeier–Haack chemistry, enabling subsequent end-group installation.
• End-group introduction: Knoevenagel condensation between the dialdehyde core and 1,1-dicyanomethylene-3-indanone (IC) affords the A–D–A motif with exocyclic C=C linkages, typically under basic catalysis (e.g., piperidine) with azeotropic water removal.
• Purification: repeated column chromatography and Soxhlet extraction (e.g., hexane → toluene → chlorobenzene) remove oligomers and polar byproducts; final product is often recrystallized from chlorinated aromatics.

Utility for chemists

• Modularity: donor core, side chains, and acceptor end groups can be varied to adjust solubility, energy levels, and morphology (e.g., ITIC-Th, ITIC-4F/IT-4F, etc.).
• Scaling considerations: minimize organotin use (prefer Suzuki over Stille when possible); implement metal-scavenging and rigorous drying to meet device-grade purity.

Target Specificity

Not applicable.

Explanation

• This product is a small-molecule semiconductor, not a biological targeting reagent (e.g., antibody, ligand, probe). No antigen/epitope specificity, clone, isotype, or species reactivity applies to ITIC.

Frequently Asked Questions

What is the purity of this product?

This product is supplied at ≥98% purity (chemical assay). Lot-specific values are stated on the Certificate of Analysis.

How should this product be stored?

Store at room temperature, protected from light. The material is light-sensitive — keep it in its original opaque or amber container.

How is this product shipped?

This product ships under standard ambient conditions. No temperature-controlled packaging is required.

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

The CAS Number is 1664293-06-4, the molecular formula is C94H82N4O2S4, and the molecular weight is 1427.94 g/mol. InChIKey HQOWCDPFDSRYRO-CDKVKFQUSA-N.

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.