The study of the solubility of naphthalene diimides with various bulky flanking substituents in different solvents by UV?vis spectroscopy

Erten, Sinan; Posokhov, Yevgen O.; Alp, Serap; İçli, Sıddık

doi:10.1016/j.dyepig.2004.04.011

Cited by 33 publications

(27 citation statements)

References 7 publications

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“…In previously reported NDI derivatives, introducing N ‐substituted flexible alkyl groups resulted in high solubility in common organic solvents. However, the derivatives showed various mesophasic phase transitions at relatively low temperatures (in some cases, about 100 °C) due to high conformational freedom and flexibility of alkyl groups . Electronic devices, including PSCs, may exhibit decreased long‐term temporal stability due to low‐temperature mesophasic phase transitions in the ETM.…”

Section: Resultsmentioning

confidence: 99%

“…However, introducing N ‐substituted wholly aromatic groups into NDI derivatives often results in low solubility in common organic solvents. This limits solution processability and, consequently, a vacuum deposition process is often used for the fabrication of electronic devices . In addition, introducing N ‐substituted bulky groups may decrease the density of semiconducting NDI cores in ETLs (i.e., decreasing electron mobility) .…”

Section: Resultsmentioning

confidence: 99%

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Nonfullerene Electron Transporting Material Based on Naphthalene Diimide Small Molecule for Highly Stable Perovskite Solar Cells with Efficiency Exceeding 20%

Jung

Heo

Lee

et al. 2018

Adv Funct Materials

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This study reports a new nonfullerene electron transporting material (ETM) based on naphthalene diimide (NDI) small molecules for use in high-performance perovskite solar cells (PSCs). These solar cells simultaneously achieve high power conversion efficiency (PCE) of over 20% and long-term stability. New NDI-ID (N,N′-Bis(1-indanyl)naphthalene-1,4,5,8-tetracarboxylic diimide) consisting of an N-substituted indane group having simultaneous alicyclic and aromatic characteristics is synthesized by a low-cost, one-step reaction, and facile purification method. The partially flexible characteristics of an alicyclic cyclopentene group on indane groups open the possibility of lowtemperature solution processing. The conformational rigidity and aromaticity of phenyl and alicyclic groups contribute to high temporal stability by strong secondary bonds. NDI-ID has herringbone packed semiconducting NDI cores that exhibit up to 0.2 cm 2 V −1 s −1 electron mobility in field effect transistors. The inverted PSCs based on CH(NH 2 ) 2 PbI 3-x Br x with NDI-ID ETM exhibit very high PCEs of up to 20.2%, which is better than that of widely used PCBM (phenyl-C61-butyric acid methyl ester) ETM-based PSCs. Moreover, NDI-IDbased PSCs exhibit very high long-term temporal stability, retaining 90% of the initial PCE after 500 h at 100 °C with 1 sun illumination without encapsulation. Therefore, NDI-ID is a promising ETM for highly efficient, stable PSCs.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Nonfullerene Electron Transporting Material Based on Naphthalene Diimide Small Molecule for Highly Stable Perovskite Solar Cells with Efficiency Exceeding 20%

Jung

Heo

Lee

et al. 2018

Adv Funct Materials

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“…Naphthalene 1,4,5,8-tetracarboxylic dianhydride (NTCDA) is the reagent of choice for obtaining diimide derivative compounds [1][2][3] . It is also used for the design and preparation of molecule-based materials (MBM`s) 4 such as molecular-electronic components, electro luminescent devices and photoconductors materials [5][6][7][8] .…”

Section: Introductionmentioning

confidence: 99%

Synthesis and properties of new paramagnetic hybrid bayerite from Al(0)/naphthalene dianhydride reaction

et al. 2010

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The reaction of Naphthalene 1,4,5,8-dianhydride (NTCDA) with elemental aluminum(0) powder is studied in an aqueous alcoholic KOH mixture to search for the NTCDA anion and dianion electron-adducts. After analyzing various reaction conditions it was found that the reaction yielded a greenish precipitate in 3:1 (v:v) ethanol:water mixture. This powder is composed mainly of aluminum trihydroxide crystallites of bayerite [a-Al(OH 3 ) (s) ] and the organic content is approximately 6%. This hybrid material proved to be paramagnetic even after exposure to air for one year and at temperatures up to 200 °C. Typical carbonylic bound to metal IR bands and reflectance UV-VIS spectra demonstrate the entrapment of NTCDA radical anion into the aluminum trihydroxide, hence rendering its green color and a paramagnetic behavior. Thus, besides the understanding of an aluminum reaction in suspension, the entrapment of an organic material (NTCDA) that stays stable as the corresponding radical can provide an interesting option for the synthesis of aluminum trihydroxide composites.

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“…Symmetrical NDIs with a long alkyl chains attached to the imide increase their solubility in organic solvents and hence facilitate the purification by column chromatography . While, the NDIs bearing aromatic or polar groups usually are purified by re‐crystallization method.…”

Section: Introductionmentioning

confidence: 99%

An Efficient Method for the Synthesis of New Non‐Symmetrical Naphthalenediimides

et al. 2018

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Herein we report an efficient synthesis of a series of nonsymmetrical naphthalenediimides (NDIs) bearing different neutral, electron-donating and electron-withdrawing groups in the imide moieties. The success of this method is based in the regioselective synthesis and isolation of pure carbamoyl naphthoic anhydride acid intermediates (CNA) in good yields (54 to 99%) and high purity, from the reaction of naphthalenetetracarboxylic dianhydride acid (NDA) with one equivalent of different primary amines and THF as solvent. The CNA intermediates were refluxed in toluene and gave the naphthalenemonoimides (NMI) in 55 to 89% yields and high purity. The N-benzyl NMI was used as starting material in the synthesis of non-symmetrical NDIs (1 a-m) in 27 to 80% yield with several amines bearing different substituted benzylic groups. In addition, this methodology was extended to obtain other new NDIs (1 n-r) in good yields (67-90%) and purity.

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The study of the solubility of naphthalene diimides with various bulky flanking substituents in different solvents by UV?vis spectroscopy

Cited by 33 publications

References 7 publications

Nonfullerene Electron Transporting Material Based on Naphthalene Diimide Small Molecule for Highly Stable Perovskite Solar Cells with Efficiency Exceeding 20%

Nonfullerene Electron Transporting Material Based on Naphthalene Diimide Small Molecule for Highly Stable Perovskite Solar Cells with Efficiency Exceeding 20%

Synthesis and properties of new paramagnetic hybrid bayerite from Al(0)/naphthalene dianhydride reaction

An Efficient Method for the Synthesis of New Non‐Symmetrical Naphthalenediimides

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