Facile synthesis of naphthalene diimide (NDI) derivatives: aggregation-induced emission, photophysical and transport properties

Kumari, Neelam; Naqvi, Samya; Ahuja, Mehak; Bhardwaj, Komal; Kumar, Rachana

doi:10.1007/s10854-020-02986-8

Cited by 24 publications

(16 citation statements)

References 49 publications

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“…These absorption peaks were found for the understudy polymers at 342/331, 360/343, and 382/364 nm corresponding to 0−2, 0−1, and 0−0 transitions, respectively, at similar wavelengths encountered for the monomeric naphthalenediimide molecules in the dilute solution. 52 A long-wavelength tail was noticed for both naphthalenediimide-based polymers spanning over the 400−600 nm range, similar to other conjugated polymers based on the same diamine. 46,53 This unresolved absorption can be associated with the ICT transitions occurring along the main chains between TPA as the donor and naphthyldiimide as the acceptor.…”

Section: Resultssupporting

confidence: 57%

“…Both P1 and P3 polyimides exhibited the signature of the naphthalene(di)imide units absorption due to the presence of their fairly well-defined vibronic absorption peaks, which suggest that the N-substitution influenced electronic transitions of the naphthalene core. These absorption peaks were found for the understudy polymers at 342/331, 360/343, and 382/364 nm corresponding to 0–2, 0–1, and 0–0 transitions, respectively, at similar wavelengths encountered for the monomeric naphthalenediimide molecules in the dilute solution …”

Section: Resultsmentioning

confidence: 55%

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Assessing the Electrical Characteristics of p–n Heterojunction Prototype Diodes Realized with n-Type Polyimide Materials

Constantin¹,

Lisă

Damaceanu³

2021

Macromolecules

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Three new aromatic polyimides with donor–acceptor topology consisting of electron-donating ortho-catenated triphenylamine (TPA) modified with two trifluoromethyl (CF3) groups and electron-accepting naphthyl(di)imide- or perylenediimide-based moieties were synthesized and thoroughly investigated. Their main physicochemical properties were assessed according to the structural variation of the dianhydride segment. The polymers exhibited advantageous solubility in polar solvents, which allowed their processing into homogeneous thin films under friendly conditions, as well as good thermal stability. The photo-optical activity investigated in detail by UV–vis and fluorescence spectroscopy was finely modulated by the electron-accepting strength of the dianhydride segment, with light emission originating from both monomeric and intramolecular charge transfer transitions, which is otherwise dependent on the polarity of the surrounding solvent molecules. Due to the high electron-accepting characteristics promoted by both CF3 and naphthyl(di)imide or perylenediimide, these polymers behaved as n-type materials. The highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) energies evaluated according to the electrochemical activity suggested the polymers suitability for use in p–n heterojunctions. Thus, to prove the electron transporting capability, prototype diodes have been realized with these polyimides in an indium tin oxide (ITO)(Al)/poly(3,4-ethylenedioxythiophene):poly(styrene sulfonate) (PEDOT:PSS)/polyimide/eGaIn configuration. Their current–voltage characteristics revealed a rectification ratio up to 63, moderate to high shunt resistance, moderate to low series resistance, and moderate current leakages. The charge transport evaluation disclosed the tunneling phenomenon as the main mechanism that drives the realized prototype diodes, with an ideality factor down to 5.48. The nice combined features encountered for these polyimides make them appealing candidates as n-type materials for advanced optoelectronic applications.

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Section: Resultssupporting

confidence: 57%

Section: Resultsmentioning

confidence: 55%

Assessing the Electrical Characteristics of p–n Heterojunction Prototype Diodes Realized with n-Type Polyimide Materials

Constantin¹,

Lisă

Damaceanu³

2021

Macromolecules

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Section: Naphthalene Diimide Derivativesmentioning

confidence: 99%

“…Naphthalene diimide (NDI) are planar π-electron deficient redox-active molecules, which makes them a popular platform for the construction of coordination polymers with ligand-based luminescence [166,167] [3,8]phenanthrolin-2-7diyl)bis-1,3-benzenedicarboxylic acid, Table 5, bib-1,4-bis(imidazol-1-yl)benzene, bibp-4,4 -bis(imidazol-1-yl)biphenyl) are presented in [168].…”

Section: Naphthalene Diimide Derivativesmentioning

confidence: 99%

Coordination Polymers Based on Highly Emissive Ligands: Synthesis and Functional Properties

et al. 2020

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Coordination polymers are constructed from metal ions and bridging ligands, linking them into solid-state structures extending in one (1D), two (2D) or three dimensions (3D). Two- and three-dimensional coordination polymers with potential voids are often referred to as metal-organic frameworks (MOFs) or porous coordination polymers. Luminescence is an important property of coordination polymers, often playing a key role in their applications. Photophysical properties of the coordination polymers can be associated with intraligand, metal-centered, guest-centered, metal-to-ligand and ligand-to-metal electron transitions. In recent years, a rapid growth of publications devoted to luminescent or fluorescent coordination polymers can be observed. In this review the use of fluorescent ligands, namely, 4,4′-stilbenedicarboxylic acid, 1,3,4-oxadiazole, thiazole, 2,1,3-benzothiadiazole, terpyridine and carbazole derivatives, naphthalene diimides, 4,4′,4′′-nitrilotribenzoic acid, ruthenium(II) and iridium(III) complexes, boron-dipyrromethene (BODIPY) derivatives, porphyrins, for the construction of coordination polymers are surveyed. Applications of such coordination polymers based on their photophysical properties will be discussed. The review covers the literature published before April 2020.

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“…In this regard, π-conjugated fused-ring systems, such as polycyclic aromatic dicarboximides [4][5][6][7] (PADI) and their heteroatom-doped analogues are emerging classes of semiconducting materials 8 derived from the well-known family of polycyclic aromatic hydrocarbons [9][10][11][12][13] (PAH). These materials have been successfully applied in organic (opto)electronics [14][15][16][17][18] and more recently, as electrodes in energy storage devices due to their remarkable redox behavior. [19][20][21][22][23] Among them, π-conjugated compounds containing imide groups, such as naphthalene 24 and perylene diimides (NDI and PDI) 1, 2, [25][26][27] are among the most successful n-type organic semiconductors, due to the strong electron-withdrawing character of the imide group, which lowers the LUMO energy levels of the semiconductor, facilitating electron injection and charge stabilization through the π-conjugated systems.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and electronic properties of nitrogen-doped π-extended polycyclic aromatic dicarboximides with multiple redox processes

et al. 2021

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Facile synthesis of naphthalene diimide (NDI) derivatives: aggregation-induced emission, photophysical and transport properties

Cited by 24 publications

References 49 publications

Assessing the Electrical Characteristics of p–n Heterojunction Prototype Diodes Realized with n-Type Polyimide Materials

Assessing the Electrical Characteristics of p–n Heterojunction Prototype Diodes Realized with n-Type Polyimide Materials

Coordination Polymers Based on Highly Emissive Ligands: Synthesis and Functional Properties

Synthesis and electronic properties of nitrogen-doped π-extended polycyclic aromatic dicarboximides with multiple redox processes

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