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.
An all-small-molecule organic solar cell derived from naphthalimide for solution-processed high-efficiency nonfullerene acceptors
Yadagiri,Narayanaswamy,Revoju, Srikanth,Eliasson, Bertil,Sharma, Ganesh D.,Singh, Surya Prakash
, p. 709 - 717 (2019)
Two small molecules BYG-1 and BYG-2 with fluorene donor and benzothiadiazole acceptor units connected to the terminal naphthamide group via ethyne linker were designed and synthesized. In this work we have discussed the effect of fluorine atoms connected with electron withdrawing benzothiadiazole unit to the fluorene core (BYG-1). In this study, we have fabricated solar cells with small-molecular donor and acceptor materials in the device architecture of bulk-heterojunction, using highly conjugated BYG-1 and BYG-2 as electron acceptors along with an appropriate small molecule donor (SMD). After improving the device architecture of the active layer using a suitable donor-to-acceptor weight ratio with solvent vapour annealing, we achieved power conversion efficiencies of 8.67% and 7.12% for BYG-1 and BYG-2, respectively. The superior photovoltaic performance of the fluorine-substituted BYG-1 can be attributed to its higher crystallinity, more balanced charge transport mobilities and efficient exciton dissociation.
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.
Designing Nonfullerene Acceptors with Oligo(Ethylene Glycol) Side Chains: Unraveling the Origin of Increased Open-Circuit Voltage and Balanced Charge Carrier Mobilities
Cui, Junjie,Park, Jung-Hwa,Kim, Dong Won,Choi, Min-Woo,Chung, Hae Yeon,Kwon, Oh Kyu,Kwon, Ji Eon,Park, Soo Young
, p. 2481 - 2488 (2021)
Despite the recent rapid development of organic solar cells (OSCs), the low dielectric constant (?r=3–4) of organic semiconducting materials limits their performance lower than inorganic and perovskite solar cells. In this work, we introduce oligo(ethylene glycol) (OEG) side chains into the dicyanodistyrylbenzene-based non-fullerene acceptors (NIDCS) to increase its ?r up to 5.4. In particular, a NIDCS acceptor bearing two triethylene glycol chains (NIDCS-EO3) shows VOC as high as 1.12 V in an OSC device with a polymer donor PTB7, which is attributed to reduced exciton binding energy of the blend film. Also, the larger size grain formation with well-ordered stacking structure of the NIDCS-EO3 blend film leads to the increased charge mobility and thus to the improved charge mobility balance, resulting in higher JSC, FF, and PCE in the OSC device compared to those of a device using the hexyl chain-based NIDCS acceptor (NIDCS-HO). Finally, we fabricate NIDCS-EO3 devices with various commercial donors including P3HT, DTS-F, and PCE11 to show higher photovoltaic performance than the NIDCS-HO devices, suggesting versatility of NIDCS-EO3.
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.
Structure-properties relationship of the derivatives of carbazole and 1,8-naphthalimide: Effects of the substitution and the linking topology
Gudeika, Dalius,Grazulevicius, Juozas Vidas,Volyniuk, Dmytro,Butkute, Rita,Juska, Gytis,Miasojedovas, Arunas,Gruodis, Alytis,Jursenas, Saulius
, p. 239 - 252 (2015)
Nine compounds having electron-accepting 1,8-naphthalimide and electron-donating carbazole moieties were synthesized employing palladium-catalyzed C-N and C-C coupling reactions and characterized by the thermal methods, absorption and emission spectrometry, electrochemical and photoelectrical tools. The synthesized compounds possess high thermal stability with the 5% weight loss temperatures being in the range of 351-476 °C. Most of the synthesized compounds are capable of glass formation with glass transition temperatures ranging from 30 to 87 °C. The cyclic voltammetry measurements showed that the solid state ionization potentials values of the carbazole and 1,8-naphthalimide derivatives range from 5.46 eV to 5.76 eV and the electron affinities values range from -3.04 eV to -2.92 eV. Dilute solutions of the 3- and 3,6-naphthalimide-substituted derivatives of carbazole in polar solvents were found to emit in the green region with quantum yields ranging from 0.66 to 0.83, while in the solid state fluorescence quantum yields were found to be in the range of 0.01-0.45. ((E)-9-(((N-(2-ethylhexyl)-1,8-naphthalimide)-4-yl)ethenyl)-9H-carbazole) exhibited efficient fluorescence in the solid state with quantum yield as high as 0.45. The effects of the linking topology of the chromophores and of the incorporated alkyl substituents on the thermal, optical, and photoelectrical properties of the synthesized donor-acceptor compounds are analyzed. The impact of the ground state intramolecular twisting of the carbazole and naphthalimide moieties induced by the substituents resulting in significant variation in the rates of radiative and nonradiative excitation deactivation is revealed.
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.
Effect of thiophene substitution on the intersystem crossing of arene photosensitizers
Sadiq, Farhan,Zhao, Jianzhang,Hussain, Mushraf,Wang, Zhijia
, p. 1794 - 1803 (2018)
The effect of thienyl substitution on the intersystem crossing (ISC) of a few arenes was studied using steady state and time-resolved transient absorption and emission spectroscopies, as well as DFT/TDDFT computations. We found that the phenyl and thienyl substituents generally induce red-shifted absorptions for the chromophores, and the DFT/TDDFT computations show that the red-shifted absorption and emission are due to the increased HOMO and the reduced LUMO energy levels. Nanosecond transient absorption spectra indicate the formation of a triplet state, the triplet state lifetime is up to 282 μs, and the singlet oxygen quantum yields (ΦΔ) are up to 60%. DFT/TDDFT computations indicate that introducing the thienyl substituent alters the relative singlet/triplet excited state energy levels, and the energy level-matched S1/T2 states are responsible for the enhanced ISC of the thienyl compounds. This information is useful for the design of heavy atom-free triplet photosensitizers and for the study of the fundamental photochemistry of organic compounds.
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)
Modular synthesis of asymmetric rylene derivatives
Sample, Caitlin S.,Goto, Eisuke,Handa, Nisha V.,Page, Zachariah A.,Luo, Yingdong,Hawker, Craig J.
, p. 1052 - 1056 (2017)
The modular synthesis of asymmetric rylenes from naphthalic anhydride derivatives is presented. Imidization, Suzuki-Miyaura coupling and cyclodehydrogenation reactions are utilized for the generation of novel functional rylenes with these three core transformations providing significant flexibility over the final structure. The combination of simple purification and high yields enables access to asymmetric rylenes with functional handles at the imide-position and site-specific incorporation of bay position substituents. The resulting library of perylenes and bisnapthalimide-anthracene derivatives showcase the presented methodology and the ability to tune optoelectronic and electrochemical properties.
