69620-20-8Relevant articles and documents
Photon upconverting liquids: Matrix-free molecular upconversion systems functioning in air
Duan, Pengfei,Yanai, Nobuhiro,Kimizuka, Nobuo
, p. 19056 - 19059 (2013)
A nonvolatile, in-air functioning liquid photon upconverting system is developed. A rationally designed triplet sensitizer (branched alkyl chain-modified Pt(II) porphyrin) is homogeneously doped in energy-harvesting liquid acceptors with a 9,10-diphenylanthracene unit. A significantly high upconversion quantum yield of ～28% is achieved in the solvent-free liquid state, even under aerated conditions. The liquid upconversion system shows a sequence of efficient triplet energy transfer and migration of two itinerant excited states which eventually collide with each other to produce a singlet excited state of the acceptor. The observed insusceptibility of upconversion luminescence to oxygen indicates the sealing ability of molten alkyl chains introduced to liquefy chromophores. The involvement of the energy migration process in triplet-triplet annihilation (TTA) provides a new perspective in designing advanced photon upconversion systems.
Design of fullerene-free electron-acceptor materials containing perylenediimide units for solution-processed organic electronic devices
Aoyagi, Koutarou,Shoji, Yu,Otsubo, Saika,Kawauchi, Susumu,Ueda, Mitsuru,Matsumoto, Hidetoshi,Higashihara, Tomoya
, p. 1083 - 1093 (2014)
Organic electron-accepting materials with light absorbance and wide absorption bands are sorely needed as alternatives to fullerene derivatives for organic electronics, in particular for organic photovoltaic (OPV) applications. In the present study, we ha
New ladder-type conjugated polymer with broad absorption, high thermal stability, and low band gap
Wang, Shitao,Hong, Wei,Ren, Shendong,Li, Jie,Wang, Mao,Gao, Xike,Li, Hongxiang
, p. 4272 - 4276 (2012)
New ladder-type π-conjugated polymer poly{6-alkyl-pyrrolo[3,2-b:4,5-b'] bis-[1,4]benzothiazine} (PPBBTZ) was synthesized through a simple method. PPBBTZ showed good solubility in organic solvents (such as chloroform, tetrahydrofuran, chlorobenzene, o-dichlorobenzene) and high thermal stability (decomposition temperatures up to 323 °C and 299 °C in nitrogen and air, respectively). The highest occupied molecular orbital and lowest unoccupied molecular orbital energy level estimated from electrochemistry result and absorption spectrum were -5.46 and -3.81 eV, respectively, with a band gap of 1.65 eV. More interestingly, PPBBTZ displayed broad absorption from ultraviolet to visible light regions (200-750 nm). These properties suggested PPBBTZ was a good candidate in opto-electronics.
Orthogonal 4,10 and 6,12 substitution of dibenzo[def,mno]chrysene polycyclic aromatic small molecules
Koldemir, Unsal,Tinkham, Jonathan S.,Johnson, Robert,Lim, Bogyu,Yemam, Henok A.,Gagnon, Kevin J.,Parkin, Sean,Sellinger, Alan
, p. 8723 - 8733 (2017)
A series of new polycyclic aromatic hydrocarbon compounds based on (4,10-disubstituted-dibenzo[def,mno]chrysene-6,12-dione) and 4,10 di-substituted 6,12-bis(triisopropylsilylethynyl)dibenzo[def,mno]chrysene are reported with tunable electronic properties
Ultralow bandgap molecular semiconductors for ambient-stable and solution-processable ambipolar organic field-effect transistors and inverters
Ozdemir, Resul,Choi, Donghee,Ozdemir, Mehmet,Kwon, Guhyun,Kim, Hyekyoung,Sen, Unal,Kim, Choongik,Usta, Hakan
, p. 2368 - 2379 (2017)
The design and development of novel ambipolar semiconductors is very crucial to advance various optoelectronic technologies including organic complementary (CMOS) integrated circuits. Although numerous high-performance ambipolar polymers have been realized to date, small molecules have been unable to provide high ambipolar performance in combination with ambient-stability and solution-processibility. In this study, by implementing highly π-electron deficient, ladder-type IFDK/IFDM acceptor cores with bithiophene donor units in D-A-D π-architectures, two novel small molecules, 2OD-TTIFDK and 2OD-TTIFDM, were designed, synthesized and characterized in order to achieve ultralow band-gap (1.21-1.65 eV) semiconductors with sufficiently balanced molecular energetics for ambipolarity. The HOMO/LUMO energies of the new semiconductors are found to be ?5.47/?3.61 and ?5.49/?4.23 eV, respectively. Bottom-gate/top-contact OFETs fabricated via solution-shearing of 2OD-TTIFDM yield perfectly ambient stable ambipolar devices with reasonably balanced electron and hole mobilities of 0.13 cm2 V?1 s?1 and 0.01 cm2 V?1 s?1, respectively with Ion/Ioff ratios of ～103-104, and 2OD-TTIFDK-based OFETs exhibit ambipolarity under vacuum with highly balanced (μe/μh ～ 2) electron and hole mobilities of 0.02 cm2 V?1 s?1 and 0.01 cm2 V?1 s?1, respectively with Ion/Ioff ratios of ～105-106. Furthermore, complementary-like inverter circuits were demonstrated with the current ambipolar semiconductors resulting in high voltage gains of up to 80. Our findings clearly indicate that ambient-stability of ambipolar semiconductors is a function of molecular orbital energetics without being directly related to a bulk π-backbone structure. To the best of our knowledge, considering the processing, charge-transport and inverter characteristics, the current semiconductors stand out among the best performing ambipolar small molecules in the OFET and CMOS-like circuit literature. Our results provide an efficient approach in designing ultralow band-gap ambipolar small molecules with good solution-processibility and ambient-stability for various optoelectronic technologies, including CMOS-like integrated circuits.
Robust Colloidal Nanoparticles of Pyrrolopyrrole Cyanine J-Aggregates with Bright Near-Infrared Fluorescence in Aqueous Media: From Spectral Tailoring to Bioimaging Applications
Yang, Cangjie,Wang, Xiaochen,Wang, Mingfeng,Xu, Keming,Xu, Chenjie
, p. 4310 - 4319 (2017)
Colloidal nanoparticles (NPs) containing near-infrared-fluorescent J-aggregates (JAGGs) of pyrrolopyrrole cyanines (PPcys) stabilized by amphiphilic block co-polymers were prepared in aqueous medium. JAGG formation can be tuned by means of the chemical structure of PPcys, the concentration of chromophores inside the polymeric NPs, and ultrasonication. The JAGG NPs exhibit a narrow emission band at 773 nm, a fluorescence quantum yield comparable to that of indocyanine green, and significantly enhanced photostability, which is ideal for long-term bioimaging.
Photocontrolled Synthesis of n-Type Conjugated Polymers
Berl, Alexandra J.,Kalow, Julia A.,Woods, Eliot F.
supporting information, p. 6062 - 6067 (2020/02/27)
Current approaches to synthesize π-conjugated polymers (CPs) are dominated by thermally driven, transition-metal-mediated reactions. Herein we show that electron-deficient Grignard monomers readily polymerize under visible-light irradiation at room temperature in the absence of a catalyst. The product distribution can be tuned by the wavelength of irradiation based on the absorption of the polymer. Conversion studies are consistent with an uncontrolled chain-growth process; correspondingly, chain extension produces all-conjugated n-type block copolymers. Preliminary results demonstrate that the polymerization can be expanded to donor–acceptor alternating copolymers. We anticipate that this method can serve as a platform to access new architectures of n-type CPs without the need for transition-metal catalysis.
A Spin-Active, Electrochromic, Solvent-Free Molecular Liquid Based on Double-Decker Lutetium Phthalocyanine Bearing Long Branched Alkyl Chains
Zielinska, Agnieszka,Takai, Atsuro,Sakurai, Hiroya,Saeki, Akinori,Leonowicz, Marcin,Nakanishi, Takashi
supporting information, p. 770 - 774 (2018/03/02)
Synthesis and characterization of a novel, multifunctional, solvent-free room-temperature liquid based on alkylated double-decker lutetium(III) phthalocyanine (Pc2Lu) are described. Lowering of the melting point and viscosity of intrinsically solid Pc2Lu compounds has been achieved through the attachment of flexible, bulky, and long branched-alkyl chains, that is, thio-2-octyldodecyl, to the periphery of the Pc2Lu unit. The embedded Pc2Lu unit maintains its inherent molecular functions, such as spin-active nature and electrochromic behavior in the liquid state. Comparison of the properties with a solid-like Pc2Lu derivative, functionalized with shorter alkyl chains, that is, thio-2-ethylhexyl, underlines the importance of the hampering effect on the π–π interactions of neighboring Pc2Lu molecules by bulkier and longer branched-alkyl chains. This study could possibly pave the way for novel multifunctional liquids whose spin-activities are associated with their rheological or optoelectronic properties.
