1193092-32-8Relevant articles and documents
Synthesis, Characterization, and Physical Properties of Pyrene-Naphthalimide Derivatives as Emissive Materials for Electroluminescent Devices
Boonnab, Sumita,Chaiwai, Chaiyon,Chitpakdee, Chirawat,Manyum, Thanaporn,Nalaoh, Phattananawee,Namuangruk, Supawadee,Promarak, Vinich,Sudyoadsuk, Taweesak
, p. 2402 - 2410 (2021)
A series of axially linked pyrene-naphthalimide fluorophores (N2Py, N4Py, and BNPy) bearing a different number of 1,8-naphthalimide units substituted on pyrene and bis-pyrene cores were designed and synthesized using palladium-catalyzed cross-coupling reactions in a stepwise synthetic manner. These molecules were chemically characterized, and their photoelectric properties were explored by spectroscopy, electrochemical and theoretical studies. They exhibited push-pull characteristics with intense fluorescence in solutions, strong solvatochromic behaviors, good thermal and electrochemical stabilities. N2Py, N4Py, and BNPy were successfully applied as emitters in solution-processed OLED devices, which resulted in blue-green emissions with promising device performance. Particularly, the BNPy-based device achieved the best EL results with a maximum brightness of 3389 cd m?2, a maximum EQE of 3.98 %, a maximum LE of 3.22 cd A?1, and a low turn-on voltage of 3.2 V.
The effect of the regioisomeric naphthalimide acetylide ligands on the photophysical properties of N^N Pt(ii) bisacetylide complexes
Liu, Lianlian,Zhang, Caishun,Zhao, Jianzhang
, p. 13434 - 13444 (2014)
Two N^N Pt(ii) bis(acetylide) complexes Pt-1 and Pt-2 with regioisomeric amino NI acetylide ligands (L-1 and L-2, L-1 = 5-amino-4-ethylnaphthaleneimide; L-2 = 3-amino-4-ethylnaphthaleneimide) were prepared. The photophysical properties of the complexes were studied by steady state and time-resolved spectroscopy. The two complexes with regioisomeric ligands (Pt-1 and Pt-2) show different photophysical properties such as maximal absorption wavelength (485 nm vs. 465 nm), triplet excited state lifetimes (23.7 μs vs. 0.9 μs), and different solvent-polarity dependences of the emission properties. The absorption of the complexes is red-shifted as compared with the previously reported Pt(ii) complex containing the 4-ethylnaphthaleneimide ligand. The two complexes with regioisomeric NI ligands were used as triplet photosensitizers for triplet-triplet annihilation (TTA) upconversion; drastically different upconversion quantum yields (15.0% vs. 1.1%) were observed. Our results are useful for designing new visible light-harvesting Pt(ii) bisacetylide complexes as triplet photosensitizers which can be used in areas such as photocatalysis, photodynamic therapy and TTA upconversion.
A naphthalimide end capped imide-fused benzothiadiazole based small molecule acceptor for organic solar cells
Lan, Liuyuan,Zhao, Baofeng,Zhang, Jie,Li, Yunchuan,Liu, Yang,Mai, Yuliang,Liao, Bing,Gao, Chao
, p. 3565 - 3571 (2019)
In this study, by incorporating imide-fused benzothiadiazole (BIBT) as the electron-withdrawing core unit, for the first time we designed and synthesized a novel A1-D-A2-D-A1 type small molecule acceptor denoted BIBT-NI for organic solar cell (OSC) applications. Its thermal, optical and electrochemical properties were thoroughly investigated. Density functional theory was also applied to shed light on the molecular configuration and energy level distribution of the acceptor. This molecule exhibited a strong absorption spectrum in the range of 420-550 nm together with an optical bandgap of 2.04 eV. The inverted OSC devices based on BIBT-NI as an electron-acceptor combined with the classical polymer poly(3-hexylthiophene) (P3HT) as an electron-donor afforded an optimal power conversion efficiency of 2.11% with a comparatively high open-circuit voltage of 0.78 V. These results underscore the promising potential of BIBT as an electron-deficient building block in constructing nonfullerene acceptors for OSCs.
Synthesis of Perylene Imide Diones as Platforms for the Development of Pyrazine Based Organic Semiconductors
De Echegaray, Paula,Manche?o, María J.,Arrechea-Marcos, Iratxe,Juárez, Rafael,López-Espejo, Guzmán,López Navarrete, J. Teodomiro,Ramos, María Mar,Seoane, Carlos,Ortiz, Rocío Ponce,Segura, José L.
, p. 11256 - 11267 (2016)
There is a great interest in peryleneimide (PI)-containing compounds given their unique combination of good electron accepting ability, high abosorption in the visible region, and outstanding chemical, thermal, and photochemical stabilities. Thus, herein we report the synthesis of perylene imide derivatives endowed with a 1,2-diketone functionality (PIDs) as efficient intermediates to easily access peryleneimide (PI)-containing organic semiconductors with enhanced absorption cross-section for the design of tunable semiconductor organic materials. Three processable organic molecular semiconductors containing thiophene and terthiophene moieties, PITa, PITb, and PITT, have been prepared from the novel PIDs. The tendency of these semiconductors for molecular aggregation have been investigated by NMR spectroscopy and supported by quantum chemical calculations. 2D NMR experiments and theoretical calculations point to an antiparallel π-stacking interaction as the most stable conformation in the aggregates. Investigation of the optical and electrochemical properties of the materials is also reported and analyzed in combination with DFT calculations. Although the derivatives presented here show modest electron mobilities of ～10-4 cm2V-1s-1, these preliminary studies of their performance in organic field effect transistors (OFETs) indicate the potential of these new building blocks as n-type semiconductors.
Reusable colorimetric and fluorescent chemosensors based on 1,8-naphthalimide derivatives for fluoride ion detection
Ding, Liang,Gao, Junkuo,Zhang, Feng,Zhang, Liang
, (2020)
Two 1, 8-naphthalimide derivatives, 2-(2-ethylhexyl)-6-(2-(4-(5-phenyl-1,3,4-oxadiazol-2-yl)benzylidene)hydrazinyl)-1H-benzo[de]isoquinoline-1,3(2H)-dione (named as NAOZ) and 2-(2-ethylhexyl)-6-(2-(4-(5-phenyl-1,3,4-thiadiazol-2-yl)benzylidene)hydrazinyl)
New Synthetic Route for Cobalt(III) Dissymmetric Bisalkynyl Complexes Based on Cobalt(III)(cyclam)(C2NAPMes)
Banziger, Susannah D.,Zeller, Matthias,Ren, Tong
, p. 4766 - 4772 (2019)
The synthesis and characterization of dissymmetric CoIII-bis-alkynyl complexes supported by cyclam (1,4,8,11-tetraazacyclotetradecane) are reported. A series of trans-[Co(cyclam)(C2NAPR)Cl]Cl were prepared from the reaction between [Co(cyclam)Cl2]Cl and HC2NAPR in the presence of Et3N, where NAPR is N-R-1,8-naphthalimide with R as mesityl (Mes, 1a), methyl (Me, 1b), 1-ethylpropyl (Pen, 1c), 2-ethylhexyl (2-ethhex, 1d), or n-octyl (Oct, 1e). Treating compounds 1a and 1b with AgOTf in NCCH3 resulted in trans-[Co(cyclam)(C2NAPR)(NCCH3)](OTf)2 (2a and 2b, respectively), while reactions with 1c, 1d and 1e under the same conditions yielded only intractable mixtures. More soluble 2a reacted further with HC2Ar in the presence of Et3N to afford trans-[Co(cyclam)(C2NAPR)(C2Ar)](OTf) with Ar as C6H4-4-NMe2 (3a), NAPMes (3b) and Ph (3c). All new complexes were characterized using X-ray diffraction (1a, 1c and 3b), IR, 1H NMR, UV/Vis and fluorescent spectroscopy, and cyclic voltammetry.
Microenvironment sensitive fluorescent organic small molecule compound as well as synthesis method and application thereof
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Paragraph 0112-0117, (2021/12/08)
The invention provides a microenvironment sensitive fluorescent organic small molecule compound as well as a synthesis method and application thereof, and a naphthalimide. As N - positions are easily substituted, the N -position is easy to be substituted, and the molecular inside generates different degrees of charge separation under the micro-environment with different polarities; 2/5 meanwhile, the maximum peak of the fluorescence emission spectrum of the - compound changes blue or D red A shift, the fluorescence intensity is changed, and the polarity sensitivity is achieved ICT.
