Quinoline-Modified Phenanthroline Electron-Transporters as n-Type Exciplex Partners for Highly Efficient and Stable Deep-Red OLEDs

Saito, Yasuhito; Sasabe, Hiroyuki; Tsuneyama, Hisaki; Abe, Shigeki; Matsuya, Misaki; Kawano, Tomoya; Kori, Yuma; Hanayama, Takanori; Kido, Junji

doi:10.1246/bcsj.20220297

Cited by 10 publications

(7 citation statements)

References 18 publications

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“…Interestingly, those conditions are tolerant to a significant number of substituents in positions 4 and 7, including aliphatic chains or aromatic rings, halogen atoms, etheroxide alcohols, and esters (Scheme 221). It is interesting to notice that carbamoylation in Harwood's conditions worked less efficiently on electronenriched phen (1051), although it was unaffected in Lee's conditions (1056).…”

Section: Action Of Organolithium Reagents On Phenmentioning

confidence: 99%

“…The halogenated (either chlorinated or brominated) compound 1114 can be involved in palladium-catalyzed Suzuki cross-coupling reactions, but there is only a limited number of examples. 1056,1057 4.3. Synthetic Methods for the Construction of phen (2,5,6,9)sub phen (2,5,6,9)sub molecules have a finely tuned coordination cavity (by sterically straining the environment around the metal center), and additional tuning can be performed by grafting substituents in positions 5 and 6, which can transmit electronic effects to the N^N cavity.…”

Section: Decoration Of the Methyl Groups Of Neocuproine Derivatives F...mentioning

confidence: 99%

“…The halogenated (either chlorinated or brominated) compound 1114 can be involved in palladium-catalyzed Suzuki cross-coupling reactions, but there is only a limited number of examples. , …”

Section: Divergent Polyfunctionalizationmentioning

confidence: 99%

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Fifty Shades of Phenanthroline: Synthesis Strategies to Functionalize 1,10-Phenanthroline in All Positions

Queffélec,

Pati,

Pellegrin

2024

Chem. Rev.

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1,10-Phenanthroline (phen) is one of the most popular ligands ever used in coordination chemistry due to its strong affinity for a wide range of metals with various oxidation states. Its polyaromatic structure provides robustness and rigidity, leading to intriguing features in numerous fields (luminescent coordination scaffolds, catalysis, supramolecular chemistry, sensors, theranostics, etc.). Importantly, phen offers eight distinct positions for functional groups to be attached, showcasing remarkable versatility for such a simple ligand. As a result, phen has become a landmark molecule for coordination chemists, serving as a must-use ligand and a versatile platform for designing polyfunctional arrays. The extensive use of substituted phenanthroline ligands with different metal ions has resulted in a diverse array of complexes tailored for numerous applications. For instance, these complexes have been utilized as sensitizers in dye-sensitized solar cells, as luminescent probes modified with antibodies for biomaterials, and in the creation of elegant supramolecular architectures like rotaxanes and catenanes, exemplified by Sauvage’s Nobel Prize-winning work in 2016. In summary, phen has found applications in almost every facet of chemistry. An intriguing aspect of phen is the specific reactivity of each pair of carbon atoms ([2,9], [3,8], [4,7], and [5,6]), enabling the functionalization of each pair with different groups and leading to polyfunctional arrays. Furthermore, it is possible to differentiate each position in these pairs, resulting in non-symmetrical systems with tremendous versatility. In this Review, the authors aim to compile and categorize existing synthetic strategies for the stepwise polyfunctionalization of phen in various positions. This comprehensive toolbox will aid coordination chemists in designing virtually any polyfunctional ligand. The survey will encompass seminal work from the 1950s to the present day. The scope of the Review will be limited to 1,10-phenanthroline, excluding ligands with more intracyclic heteroatoms or fused aromatic cycles. Overall, the primary goal of this Review is to highlight both old and recent synthetic strategies that find applicability in the mentioned applications. By doing so, the authors hope to establish a first reference for phenanthroline synthesis, covering all possible positions on the backbone, and hope to inspire all concerned chemists to devise new strategies that have not yet been explored.

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Section: Action Of Organolithium Reagents On Phenmentioning

confidence: 99%

Section: Decoration Of the Methyl Groups Of Neocuproine Derivatives F...mentioning

confidence: 99%

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Fifty Shades of Phenanthroline: Synthesis Strategies to Functionalize 1,10-Phenanthroline in All Positions

Queffélec,

Pati,

Pellegrin

2024

Chem. Rev.

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“…This can be converted to a bottom–up approach through introducing nanoarchitectonics at dynamic interfaces. In this case, many functional molecules and their supramolecular structures will be used for device fabrication [ 426 , 427 , 428 , 429 , 430 ]. Recently, Ishii, Yamashita, and co-workers have developed a chemical doping technique based on the redox reaction of benzoquinone and hydroquinone in an aqueous solution under ambient conditions [ 431 ].…”

Section: Summary and Perspectivesmentioning

confidence: 99%

Materials Nanoarchitectonics at Dynamic Interfaces: Structure Formation and Functional Manipulation

Ariga

2024

Materials

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The next step in nanotechnology is to establish a methodology to assemble new functional materials based on the knowledge of nanotechnology. This task is undertaken by nanoarchitectonics. In nanoarchitectonics, we architect functional material systems from nanounits such as atoms, molecules, and nanomaterials. In terms of the hierarchy of the structure and the harmonization of the function, the material created by nanoarchitectonics has similar characteristics to the organization of the functional structure in biosystems. Looking at actual biofunctional systems, dynamic properties and interfacial environments are key. In other words, nanoarchitectonics at dynamic interfaces is important for the production of bio-like highly functional materials systems. In this review paper, nanoarchitectonics at dynamic interfaces will be discussed, looking at recent typical examples. In particular, the basic topics of “molecular manipulation, arrangement, and assembly” and “material production” will be discussed in the first two sections. Then, in the following section, “fullerene assembly: from zero-dimensional unit to advanced materials”, we will discuss how various functional structures can be created from the very basic nanounit, the fullerene. The above examples demonstrate the versatile possibilities of architectonics at dynamic interfaces. In the last section, these tendencies will be summarized, and future directions will be discussed.

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“…Functional materials must be created to meet these needs. These include generating energy [1][2][3][4][5][6][7], storing energy [8][9][10][11][12][13], detecting and removing environmental hazards [14][15][16][17][18][19], carbon neutrality [20][21][22][23], purifying water [24][25][26][27][28], detecting and handling viruses [29][30][31][32][33], delivering drugs [34][35][36][37][38], treating illness and injury [39][40][41][42][43][44], developing devices for these functions [45][46][47][48][49], and information conversion…”

Section: Introductionmentioning

confidence: 99%

Confined Space Nanoarchitectonics for Dynamic Functions and Molecular Machines

Ariga

2024

Micromachines

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Nanotechnology has advanced the techniques for elucidating phenomena at the atomic, molecular, and nano-level. As a post nanotechnology concept, nanoarchitectonics has emerged to create functional materials from unit structures. Consider the material function when nanoarchitectonics enables the design of materials whose internal structure is controlled at the nanometer level. Material function is determined by two elements. These are the functional unit that forms the core of the function and the environment (matrix) that surrounds it. This review paper discusses the nanoarchitectonics of confined space, which is a field for controlling functional materials and molecular machines. The first few sections introduce some of the various dynamic functions in confined spaces, considering molecular space, materials space, and biospace. In the latter two sections, examples of research on the behavior of molecular machines, such as molecular motors, in confined spaces are discussed. In particular, surface space and internal nanospace are taken up as typical examples of confined space. What these examples show is that not only the central functional unit, but also the surrounding spatial configuration is necessary for higher functional expression. Nanoarchitectonics will play important roles in the architecture of such a total system.

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Quinoline-Modified Phenanthroline Electron-Transporters as n-Type Exciplex Partners for Highly Efficient and Stable Deep-Red OLEDs

Cited by 10 publications

References 18 publications

Fifty Shades of Phenanthroline: Synthesis Strategies to Functionalize 1,10-Phenanthroline in All Positions

Fifty Shades of Phenanthroline: Synthesis Strategies to Functionalize 1,10-Phenanthroline in All Positions

Materials Nanoarchitectonics at Dynamic Interfaces: Structure Formation and Functional Manipulation

Confined Space Nanoarchitectonics for Dynamic Functions and Molecular Machines

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