4-(2,3-Dihydro-1,3-dimethyl-1H-benzimidazol-2-yl)-N,N-dimethylbenzenamine

• CAS: 302818-73-1
• Catalog Number: ACM302818731-1
• Category: Main Products
• Molecular Weight: 267.37
• Molecular Formula: C17H21N3
• Description: 4-(2,3-Dihydro-1,3-dimethyl-1H-benzimidazol-2-yl)-N,N-dimethylbenzenamine is a semiconducting organic molecule with a π-conjugated polycyclic system. It is a strong electron donor molecule that can be used for n-type doping. It shows conductivity of ~2 × 10-3 S/cm as a dopant. It also acts as a reagent for the reductive transformation of organic compounds.
• Synonyms: 4-(1,3-Dimethyl-2,3-dihydro-1H-benzoimidazol-2-yl)phenyl)dimethylamine,N-DMBI
• IUPAC Name: 4-(1,3-dimethyl-2H-benzimidazol-2-yl)-N,N-dimethylaniline
• SMILES: CN(C)c1ccc(cc1)C2N(C)c3ccccc3N2C
• InChI: 1S/C17H21N3/c1-18(2)14-11-9-13(10-12-14)17-19(3)15-7-5-6-8-16(15)20(17)4/h5-12,17H,1-4H3,AKIIMLCQTGCWQQ-UHFFFAOYSA-N
• InChI Key: AKIIMLCQTGCWQQ-UHFFFAOYSA-N
• Melting Point: 105-110 °C
• Appearance: Light orange powder
• Application: Air stable n-type dopant for n-channel Organic Thin Film Transistors (OTFTs) and solar cells (OPVs).
• Storage: room temp
• Assay: 98% (HPLC)
• Complexity: 304
• Covalently-Bonded Unit Count: 1
• Exact Mass: 267.173548g/mol
• Formal Charge: 0
• H-Bond Acceptor: 3
• H-Bond Donor: 0
• Heavy Atom Count: 20
• MDL Number: MFCD00222361
• Monoisotopic Mass: 267.173548g/mol
• Packaging: 1 g in glass bottle
• Quality Level: 100
• Rotatable Bond Count: 2
• XLogP3: 3.7

Case Study

Tuning Acene Core Size in Ladder-Type Polymers for Enhanced n-Type Thermoelectric Performance with N-DMBI Doping

Chen, Hu, et al. Journal of the American Chemical Society 143.1 (2020): 260-268.

Three fused lactam ladder-type conjugated polymers with systematically varied acene core sizes (ranging from all-naphthalene to mixed naphthalene-anthracene to all-anthracene backbones) were synthesized and doped with N-DMBI to explore structure-property relationships in n-type thermoelectrics.
Experimental Protocol: Polymers were synthesized via acid-catalyzed aldol polycondensation of bis-oxindole and bis-isatin monomers, yielding high molecular weights exceeding 50 kDa. Thin films were doped with N-DMBI at ratios from 3 to 25 mol% using solution-based processing. Energy levels were characterized by ultraviolet photoelectron spectroscopy, low-energy inverse photoemission spectroscopy, and UV-vis-NIR absorption. Charge transport was evaluated in organic field-effect transistors, and thermoelectric properties including electrical conductivity and Seebeck coefficient were measured as a function of dopant concentration. Density functional theory calculations complemented the experimental data.
Performance Evaluation: The all-naphthalene polymer achieved the highest electrical conductivity of 0.65 S/cm and a power factor of 3.2 microwatt/(m*K²) when doped with N-DMBI, ranking among the top reported values for n-type polymers. Expanding the acene core progressively raised the lowest unoccupied molecular orbital energy and reduced polaron delocalization, as confirmed by theoretical calculations. All polymers exhibited exceptional thermal stability with decomposition temperatures exceeding 360 degrees Celsius, confirming their suitability for thermoelectric device applications.

N-DMBI Molecular Doping Unlocks Record Electron Mobility in Non-Fullerene Acceptor O-IDTBR

Paterson, Alexandra F., et al. Journal of Materials Chemistry C 9.13 (2021): 4486-4495.

Non-fullerene acceptors have revolutionized organic photovoltaics, yet their application in n-type transistors has been limited by the scarcity of effective molecular dopants. This study demonstrates that N-DMBI, along with two other n-dopants, can dramatically enhance electron transport in the small-molecule semiconductor O-IDTBR through a synergistic combination of electronic doping and beneficial microstructural reorganization.
Experimental Protocol: O-IDTBR thin films were doped with N-DMBI at various molar percentages in chlorobenzene solution, then spin-coated as the active layer in top-gate bottom-contact transistors. Electron paramagnetic resonance spectroscopy confirmed successful charge transfer. Grazing-incidence wide-angle X-ray scattering revealed dopant-induced changes in molecular packing orientation. Atomic force microscopy characterized film morphology, while molecular dynamics simulations and kinetic Monte Carlo calculations modeled charge transport anisotropy.
Performance Evaluation: N-DMBI doping boosted electron mobility to values exceeding 1 cm²/(V*s), among the highest reported for non-fullerene acceptor molecules. Critically, the dopant induced a previously unreported [020] crystallographic orientation that favored charge transport along the substrate plane. Electron paramagnetic resonance confirmed n-type doping activity, while theoretical simulations revealed that the mobility tensor is highly anisotropic with the largest component oriented favorably in the new packing arrangement. The study establishes dopant-induced morphology modification as a powerful and underexplored mechanism for enhancing charge transport in organic semiconductors.

Solution-Phase Polarity Engineering of Carbon Nanotube Transistors via N-DMBI Additive Blending

Salazar-Rios, Jorge Mario, et al. Advanced Electronic Materials 6.3 (2020): 1900789.

Semiconducting single-walled carbon nanotubes hold promise for next-generation logic circuits, yet their intrinsically ambipolar transport behavior must be converted to unipolar operation for practical complementary logic. A straightforward ink-blending approach using molecular additives including N-DMBI was developed to control transistor polarity without requiring additional fabrication steps or post-deposition treatments.
Experimental Protocol: Highly purified semiconducting nanotube inks were prepared by polymer wrapping with either poly(3-dodecylthiophene) or a polyfluorene derivative. N-DMBI was dissolved in the ink solvent and mixed with the nanotube dispersion at controlled concentrations. Field-effect transistors were fabricated in both coplanar and staggered configurations on silicon dioxide dielectrics. Transfer line method measurements quantified contact resistance, while optical spectroscopy including steady-state and time-resolved photoluminescence probed dopant-nanotube interactions.
Performance Evaluation: N-DMBI incorporation converted ambipolar transistors with mobility around 0.7 cm²/(V*s) into unipolar n-type devices achieving electron mobility up to 4.2 cm²/(V*s) with a near-zero threshold voltage. In the staggered transistor configuration that eliminates surface trap effects, N-DMBI-treated devices reached 9.0 cm²/(V*s). The mechanism was attributed to genuine molecular doping of the active channel rather than work function modification, as evidenced by the concurrent increase in mobility and threshold voltage shift without significant contact resistance reduction. The doping efficiency was found to be mediated by the wrapping polymer layer surrounding the nanotubes.

Custom Q&A

What is the molecular formula of the compound?

The molecular formula of the compound is C17H21N3.

What are the synonyms of the compound?

The synonyms of the compound are 302818-73-1, GNF-Pf-4385, 1,3-Dimethyl-2-phenyl-2,3-dihydro-1H-benzoimidazole, and 4-(1,3-dimethyl-2H-benzimidazol-2-yl)-N,N-dimethylaniline.

What is the molecular weight of the compound?

The molecular weight of the compound is 267.37 g/mol.

When was the compound created?

The compound was created on July 8, 2005.

When was the compound last modified?

The compound was last modified on October 21, 2023.

What is the IUPAC name of the compound?

The IUPAC name of the compound is 4-(1,3-dimethyl-2H-benzimidazol-2-yl)-N,N-dimethylaniline.

What is the InChI of the compound?

The InChI of the compound is InChI=1S/C17H21N3/c1-18(2)14-11-9-13(10-12-14)17-19(3)15-7-5-6-8-16(15)20(17)4/h5-12,17H,1-4H3.

What is the InChIKey of the compound?

The InChIKey of the compound is AKIIMLCQTGCWQQ-UHFFFAOYSA-N.

What is the Canonical SMILES of the compound?

The Canonical SMILES of the compound is CN1C(N(C2=CC=CC=C21)C)C3=CC=C(C=C3)N(C)C.

What is the CAS number of the compound?

The CAS number of the compound is 302818-73-1.