Comparative study of long alkyl chain substituted naphthalene diimide derivatives as n-type organic thin-film transistor materials

Ichikawa, Musubu; Iwasaki, Katsunori; Ohyama, Atsuro; Miyazawa, J.; Yokota, Yoichiro; Hirata, Naoki; Oguma, Naomi

doi:10.7567/jjap.56.111601

Cited by 13 publications

(14 citation statements)

References 32 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Solution-processed, linear alkyl-substituted NDIs exhibit relatively high field-effect electron mobilities (μ e ), reportedly reaching almost 0.2 cm 2 V −1 s −1 [ 17 , 42 , 50 , 70 , 71 ]. The μ e for NDIC8 (studied in this work) can reach 0.16 cm 2 V −1 s −1, whereas longer-chain NDIs tend to reveal lower mobilities: μ e for NDIC12 and NDIC18 (not included in the NDI range in this work) were reported to be 0.01 and 0.005 cm 2 V −1 s −1 , respectively [ 42 , 72 ].…”

Section: Resultsmentioning

confidence: 99%

“…Despite a proven potential in the field of electronic and energy materials as n-type semiconductors [ 54 ], a survey of the literature reveals that a complete comparative study of their electronic properties is still lacking. Analysis of the scattered published data indicates, for instance, that the effect of the alkyl chain length cannot be unequivocally identified based on previous studies mainly because of different methodologies used in different works [ 51 , 70 ]. Hence, in our work, we performed unified tests of electron field mobility using organic field-effect transistors (OFETs) as diagnostic devices.…”

Section: Resultsmentioning

confidence: 99%

See 1 more Smart Citation

Synthesis, Solution, and Solid State Properties of Homological Dialkylated Naphthalene Diimides—A Systematic Review of Molecules for Next-Generation Organic Electronics

et al. 2023

View full text Add to dashboard Cite

This systematic study aimed at finding a correlation between molecular structure, solubility, self-assembly, and electronic properties of a homological series of N-alkylated naphthalene diimides (NDIs). NDIs are known for their n-type carrier mobility and, therefore, have potential in the field of organic electronics, photovoltaics, and sensors. For the purpose of this study, nine symmetrical N,N′-dialkylated naphthalene diimides (NDIC3-NDIC11) were synthesized in the reaction of 1,4,5,8-naphthalenetetracarboxylic dianhydride with alkylamines ranging from propyl- to undecyl-. The NDIs were characterized by spectroscopic (NMR, UV-Vis, FTIR), microscopic, and thermal methods (TGA and DSC), and X-ray diffraction (XRD). Our experimental study, extensively referring to findings reported in the literature, indicated that the NDIs revealed specific trends in spectroscopic and thermal properties as well as solubility and crystal morphology. The solubility in good solvents (chloroform, toluene, dichlorobenzene) was found to be the highest for the NDIs substituted with the medium-length alkyl chains (NDIC5–NDIC8). Systematic FTIR and XRD studies unraveled a distinct parity effect related to the packing of NDI molecules with odd or even numbers of methylene groups in the alkyl substituents. The NDIs with an even number of methylene groups in the alkyl substituents revealed low-symmetry (P1−) triclinic packing, whereas those with an odd number of carbon atoms were generally monoclinic with P21/c symmetry. The odd–even parity effect also manifested itself in the overlapping of the NDIs’ aromatic cores and, hence, the π-π stacking distance (dπ-π). The odd-numbered NDIs generally revealed slightly smaller dπ-π values then the even-numbered ones. Testing the NDIs using standardized field-effect transistors and unified procedures revealed that the n-type mobility in NDIC6, NDIC7, and NDIC8 was 10- to 30-fold higher than for the NDIs with shorter or longer alkyl substituents. Our experimental results indicate that N,N′-alkylated NDIs reveal an optimum range of alkyl chain length in terms of solution processability and charge transport properties.

show abstract

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Synthesis, Solution, and Solid State Properties of Homological Dialkylated Naphthalene Diimides—A Systematic Review of Molecules for Next-Generation Organic Electronics

et al. 2023

View full text Add to dashboard Cite

show abstract

“…Recently, the hole mobility of the p-type organic semiconductor was observed to be above 10 cm 2 V –1 s –1 in the 2D electronic π-band structure, , wherein weak van der Waals interactions such as S···S, S···N, C–H···π, and S···π contacts as well as π-stacking interactions play an important role in increasing the electronic dimensionality. − For instance, oligothiophene, TTF, benzothieno[3,2- b ]benzothiophene (BTBT), and dinaphtho[2,3-b:2′,3′-f]thieno[3,2- b ]thiophene (DNTT) have been utilized as high-performance p-type semiconducting materials. − On the contrary, excellent 2D electronic π-band structures are usually challenging to design using electron transport n-type semiconducting materials based on planar π-molecules. − In addition, chemically stable n-type organic semiconductors operating in air are limited in number . Among them, nitrogen-containing π-planar molecules such as naphthalenediimide ( NDI ), perylenediimide ( PDI ), and azaacene derivatives have been widely utilized in n-type semiconducting materials. − Chemical control of the dimensionality and π-electron density in molecular crystals can help design high-performance n-type semiconductors such as NDI and PDI π-frameworks. Herein, we focused on the strong electrostatic interactions between the dianionic NDI and simple cations to form cation–anion pairs in organic salts …”

Section: Introductionmentioning

confidence: 99%

Density and Dimensional Control of π-Electrons in Electrostatically Binding Naphthalenediimide Salts

Kawasaki

Takeda

Hoshino

et al. 2020

Crystal Growth & Design

View full text Add to dashboard Cite

Dianionic bis(benzenesulfonate)–naphthalenediimide (BSNDI 2– ) formed simple 2:1 cation–anion salts of (NH4 +)2(BSNDI 2– ) (1), (CH3NH3 +)2(BSNDI 2– ) (2), (C2H5NH3 +)2(BSNDI 2– ) (3), [(C2H5)2NH2 +]2(BSNDI 2– ) (4), and [(C2H5)3NH+]2(BSNDI 2– ) (5). The thermal stability, crystal structure, electron transport properties, and dielectric response were evaluated for these systems in terms of π-electron density and dimensional crossover from two-dimensional (2D) and one-dimensional (1D) to zero-dimensional (0D) electronic structures. Systematic modification of the counter cations from NH4 + to simple alkylammoniums (CH3NH3 +, C2H5NH3 +, (C2H5)2NH2 +, and (C2H5)3NH+) for BSNDI 2– salts affected the packing π-density and dimensionality of NDI π-cores. All single crystals formed alternating cation–anion layers, where the intermolecular interactions in salts 1, 2, 3, 4, and 5 were observed as dense 2D brickstone, 1D column, 1D column, dilute 2D herringbone, and isolated 0D monomer arrangements, respectively. The π-electron occupation percentage in the unit cell of salts 1, 2, 3, 4, and 5 decreased in that order, at 96.2%, 87.8%, 83.8%, 78.8%, and 72.6%, respectively, where the intermolecular π–π interaction between BSINDI 2– anions was gradually diluted on increasing in the cation volume. The transfer integrals between the lowest unoccupied molecular orbital in salts 1–5 clearly indicated a dimensional crossover from 2D to 1D to 0D electronic structures. Flash-photolysis time-resolved microwave conductivity measurements of salts 1, 2, 3, and 4 helped determine the magnitude of electron carrier mobility, which followed the order 1 > 2 ≈ 3 ≈ 4. The dielectric response of salt 1 being an order of magnitude higher than those of salts 2–5 was associated with the protonic conductivity in the NH4 +···–SO3– electrostatic hydrogen-bonding network layer. Simple cation exchange in dianionic BSNDI 2– salts conventionally modified the intermolecular π–π interactions in terms of dimensionality, magnitude, and electron transport properties.

show abstract

“…The simple π-molecular framework of electron-accepting NDI was utilized for introducing the ion-pairing unit of benzenesulfonate (−C 6 H 4 –SO 3 – ) to form a dianionic π-molecular core. The π-electronic structure of NDI has been widely applied to air-stable n-type organic semiconductors, − unidimensional self-assemblies, , spin fluctuation magnets, , metal–organic frameworks, and fluorescent sensor molecules, , where quite high electronic mobilities (∼8.6 cm 2 V –1 s –1 ) have been reported for the chlorinated NDI π core . Although the preparation of (Na + ) 2 ( BSNDI 2– ) has been already reported by Miller et al, there is no information currently available about its thermal property, crystal structure, dielectric response, and electron transport property …”

Section: Introductionmentioning

confidence: 99%

High Thermally Stable n-Type Semiconductor up to 850 K Based on Dianionic Naphthalenediimide Derivative

et al. 2019

View full text Add to dashboard Cite

Electrostatic cation–anion interaction is effective to form a tightly bounded π-molecular assembly, which enhances the thermal stability and carrier transport property. Dianionic bis(benzenesulfonate)–naphthalenediimide (BSNDI 2– ) formed simple 2:1 cation–anion pairs of (Na+)2(BSNDI 2– ) (1), (K+)2(BSNDI 2– ) (2), and (NH4 +)2(BSNDI 2– ) (3), and their redox behaviors, thermal stabilities, crystal structures, electron transport properties, and dielectric constants were compared to those of neutral bis(phenyl)–naphthalenediimide (4). Crystals 1, 2, and 3 had quite high thermal stabilities up to 850, 810, and 600 K, respectively, even though organic molecules. A two-dimensional (2D) n-type electron transport layer consisting of NDI π cores was sandwiched between networks of highly polarized electrostatic cation–anion pairs showing 2D herringbone (1), one-dimensional π-stacking (2), and brickstone-like 2D π-stacking (3) interactions. The values of electron mobility in polycrystalline 1, 2, 3, and 4 reached 0.22, >0.0003, 0.036, and >0.028 cm2 V–1 s–1, respectively, according to flash-photolysis time-resolved microwave conductivity measurements. The electron mobility of crystal 1 was 1 order of magnitude higher than those of crystals 2, 3, and 4 owing to the tight intermolecular interactions within the 2D transport layer. The real part dielectric constants of crystals 1, 2, 3, and 4 were ∼4, ∼50, ∼20, and ∼4 at 450 K, respectively, which affected the electron transport property. The chemical design of highly polarized electrostatic cation–anion pair formed the 2D transport layer and also has high thermal stability up to ∼850 K in the ionic n-type semiconducting materials.

show abstract

Comparative study of long alkyl chain substituted naphthalene diimide derivatives as n-type organic thin-film transistor materials

Cited by 13 publications

References 32 publications

Synthesis, Solution, and Solid State Properties of Homological Dialkylated Naphthalene Diimides—A Systematic Review of Molecules for Next-Generation Organic Electronics

Synthesis, Solution, and Solid State Properties of Homological Dialkylated Naphthalene Diimides—A Systematic Review of Molecules for Next-Generation Organic Electronics

Density and Dimensional Control of π-Electrons in Electrostatically Binding Naphthalenediimide Salts

High Thermally Stable n-Type Semiconductor up to 850 K Based on Dianionic Naphthalenediimide Derivative

Contact Info

Product

Resources

About