One-pot synthesis of 2-bromo-4,5-diazafluoren-9-one via a tandem oxidation–bromination-rearrangement of phenanthroline and its hammer-shaped donor–acceptor organic semiconductors

Zhao, Jianfeng; Lin, Chin‐Wen; Sun, Pengju; Hou, Xiaofan; Zhao, Xiang-Hua; Li, Weijie; Xie, Linghai; Qian, Yan; Shi, Nai; Lai, Wen‐Yong; Fan, Quli

doi:10.1016/j.tet.2010.12.065

Cited by 32 publications

(12 citation statements)

References 53 publications

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“…Photoluminescence spectra in several different polar solvents were also measured and shown in Figure S6 (Supporting Information). Three diazafluorene derivatives exhibited obviously solvent‐dependent fluorescence that is the higher polarity of the solvent, the more pronounced red‐shift of the emission maxima, indicating the complicated excited states and energy transfer occur . With increased concentration in solutions, hypsochromic shifts of emission peaks were also found, and TPA(PDAF) 3 showed the smallest change (Figure b).…”

Section: Resultsmentioning

confidence: 97%

“…The synthesis routes of tertiary alcohols and TPA(PDAF) n ( n = 1, 2, 3) are listed in Scheme (route I and route II). 4,5‐diazafluorene‐9‐one (DAFO) was prepared as precious works in our group . Owing to the strong electron‐deficiency of two pyridine rings, 1,8‐position of DAFO is activated enough to occur michael addition reaction under the attack of grignard reagent.…”

Section: Resultsmentioning

confidence: 99%

“…Tetrahydrofuran (THF) and toluene were dried over sodium benzophenone ketyl anion radical and distilled under a dry nitrogen atmosphere immediately prior to use. DAFO was synthesized as in our previous work . Pentacene, PS (weight average molecular weight, M w = 250 000) were purchased from Sigma‐Aldrich and used without further purification.…”

Section: Methodsmentioning

confidence: 99%

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4,5‐Diazafluorene‐Based Donor–Acceptor Small Molecules as Charge Trapping Elements for Tunable Nonvolatile Organic Transistor Memory

Bian

Chen

et al. 2018

Advanced Science

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Three diazafluorene derivatives triphenylamine (TPA)(PDAF)n (n = 1, 2, 3) serving as small molecular elements are designed and synthesized via concentrated sulfuric acid mediated Friedel–Crafts reaction. With highly nonplanar topological configuration, TPA(PDAF)3 shows weaker intermolecular interaction in the solid states and thus exhibits single nanomolecular behavior, which is crucial for charge stored and retained in an organic field‐effect transistor (OFET) memory device. Furthermore, diazafluorene derivatives possess a completely separate highest occupied molecular orbital/lowest unoccupied molecular orbital, which offers ideal hole and electron trapping sites. As charge storage elements, triphenylamine groups provide the hole trapping sites, while diazafluorene units provide the electron trapping sites and act as a hole blocking group to restrain the leakage of stored holes trapped in triphenylamine. The pentacene‐based OFET memory device with solution‐processing TPA(PDAF)3 shows a good hole‐trapping ability, high hole trapping density (4.55 × 1012 cm−2), fast trapping speed (<20 ms), a large memory window (89 V), and a tunable ambipolar memory behavior. The optimized device shows a large ON/OFF current ratio (2.85 × 107), good charge retention (>104 s), and reliable endurance properties. This study suggests that diazafluorene based donor–acceptor small molecular elements have great promise for high‐performance OFET memory.

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Section: Resultsmentioning

confidence: 97%

Section: Resultsmentioning

confidence: 99%

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4,5‐Diazafluorene‐Based Donor–Acceptor Small Molecules as Charge Trapping Elements for Tunable Nonvolatile Organic Transistor Memory

Bian

Chen

et al. 2018

Advanced Science

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“…2.1.1. 3-Bromo-1,10-phenantroline-5,6-dione (Br-phendione) and 3,8-Dibromo-1,10-phenantroline-5,6-dione (diBr-phendione) Bromo derivatives of phendione were prepared according to the modified literature procedure [40]. 1,10-phenantroline-5,6-dione (phendione) (20 g, 95.2 mmol) was dissolved in a chilled mixture of 120 mL 98% H 2 SO 4 and 60 mL 99% HNO 3 in a 500 mL round-bottom flask.…”

Section: Synthesesmentioning

confidence: 99%

Bis(triphenylphosphine)iminium Salts of Dioxothiadiazole Radical Anions: Preparation, Crystal Structures, and Magnetic Properties

2019

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Phenanthroline dioxothiadiazoles are redox active molecules that form stable radical anions suitable for the construction of supramolecular magnetic materials. Herein, the preparation, structures and magnetic properties of bis(triphenylphosphine)iminium (PPN) salts of [1,2,5]thiadiazole[3,4-f][1,10]phenanthroline 1,1-dioxide (L), [1,2,5]thiadiazole[3,4-f][4,7]phenanthroline 1,1-dioxide (4,7-L), 5-bromo-[1,2,5]thiadiazolo[3,4-f][1,10]phenanthroline 2,2-dioxide (BrL), and 5,10-dibromo-[1,2,5]thiadiazolo[3,4-f][1,10]phenanthroline 2,2-dioxide (diBrL) are reported. The preparation of new bromo derivatives of the L: 5-bromo-[1,2,5]thiadiazolo[3,4-f][1,10]phenanthroline 2,2-dioxide (BrL) and 5,10-dibromo-[1,2,5]thiadiazolo[3,4-f][1,10]phenanthroline 2,2-dioxide (diBrL)—suitable starting materials for further derivatization—are described starting from a commercially available and cheap 1,10-phenanthroline. All PPN salts show antiferromagnetic interactions between the pairs of radical anions, which in the case of PPN(diBrL) are very strong (−116 cm−1; using Ĥ = −2JSS type of exchange coupling Hamiltonian) due to a different crystal packing of the anion radicals as compared to PPN(L), PPN(4,7-L), and PPN(BrL).

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“…The multi-levelled molecular substructures of PF derivatives, such as dialkylfluorenes (F-I), heterofluorenes (F-II) [32][33][34], fused or curved fluorenes (F-III) [35], diarylfluorenes (F-IV) [36,37] and spirofluorenes (F-V) [38,39] (figure 1), have become an ideal platform to demonstrate the four-element principle that contains the p-n covalent design (also called the D-A design) [40][41][42][43], steric design [44,45], conformation and topology design [15,[46][47][48] and supramolecular interaction [25,31,49,50]. Previously, many efforts have been made to clarify low-energy green emission bands (also called g-bands) in PF-based electroluminescent thin films for application in high-performance devices [86].…”

Section: Introductionmentioning

confidence: 99%

Fluorene-based macromolecular nanostructures and nanomaterials for organic (opto)electronics

Xie

Yang

Lin

et al. 2013

Phil. Trans. R. Soc. A.

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Nanotechnology not only opens up the realm of nanoelectronics and nanophotonics, but also upgrades organic thin-film electronics and optoelectronics. In this review, we introduce polymer semiconductors and plastic electronics briefly, followed by various top-down and bottom-up nano approaches to organic electronics. Subsequently, we highlight the progress in polyfluorene-based nanoparticles and nanowires (nanofibres), their tunable optoelectronic properties as well as their applications in polymer light-emitting devices, solar cells, field-effect transistors, photodetectors, lasers, optical waveguides and others. Finally, an outlook is given with regard to four-element complex devices via organic nanotechnology and molecular manufacturing that will spread to areas such as organic mechatronics in the framework of robotic-directed science and technology.

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One-pot synthesis of 2-bromo-4,5-diazafluoren-9-one via a tandem oxidation–bromination-rearrangement of phenanthroline and its hammer-shaped donor–acceptor organic semiconductors

Cited by 32 publications

References 53 publications

4,5‐Diazafluorene‐Based Donor–Acceptor Small Molecules as Charge Trapping Elements for Tunable Nonvolatile Organic Transistor Memory

4,5‐Diazafluorene‐Based Donor–Acceptor Small Molecules as Charge Trapping Elements for Tunable Nonvolatile Organic Transistor Memory

Bis(triphenylphosphine)iminium Salts of Dioxothiadiazole Radical Anions: Preparation, Crystal Structures, and Magnetic Properties

Fluorene-based macromolecular nanostructures and nanomaterials for organic (opto)electronics

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