548-35-6Relevant academic research and scientific papers
Design and synthesis of highly twisted phenanthroimidazole substituted blue-emitting truxene based fluorescent chromophores
Kaur, Banpreet,Moghe, Dhanashree,Kabra, Dinesh,Jacob, Josemon
, p. 2278 - 2288 (2019)
The modified Debus-Radziszewski reaction was used to design and synthesize novel truxene derived blue-emitting materials bearing phenanthroimidazole substituents. The materials were prepared non-catalytically under ambient conditions using a triamino based derivative of truxene as a key precursor in good yields. The 5, 5′, 10, 10′, 15, and 15′ positions of the truxene were alkylated to provide solubility to the molecules, making the materials solution processable. The substituted phenanthroimidazole moieties were introduced at the 2, 7, 12 positions of truxene to synthesize the target molecules. Three new materials were prepared by varying the phenyl group attached at the C2 position of the phenanthroimidazole moiety, designated as PT1 for the phenyl, PT2 for the 4-methoxyphenyl, and PT3 for the 4-cyanophenyl substituent. From the photophysical studies, PT3 was found to have dominant charge transfer characteristics in its excited state. Also, PT3 exhibited a photoluminescence quantum yield as high as 0.83. The optimized geometries from the computational studies revealed that the molecules are highly twisted, with dihedral angles of ～75°. The HOMO-LUMO distributions were found to be well separated showing the bipolar characteristic of the compounds. The band gap values from computational studies were found to be in agreement with experimental values. The emission spectra in the solid state gave maxima at 402 nm for PT1, 412 nm for PT2, and 450 nm for PT3. The materials were thus found to be emitting in the blue region of the visible spectrum. The TCSPC and TRPL studies were carried out to explore further the excited states of the molecules, wherein radiative pathways were found to be dominant.
Synthesis and photophysical properties of star-shaped blue green emitting π-conjugated spirotruxenes
Kotha, Sambasivarao,Ali, Rashid,Panguluri, Nageswara Rao,Datta, Anindya,Kannaujiya, Krishna K.
, p. 4080 - 4085 (2018)
Here, we report a simple and useful strategy for a series of C3-symmetric π-conjugated and highly soluble spiro-annulated truxene derivatives. The role of substituent at C5, C10, C15, C2, C7, and C12 positions was studied. We observed that truxenes containing carbonyl groups showed red shift in the absorption maxima in comparison with compounds devoid of carbonyl group. Enhanced conjugation in these systems may be responsible for this red shift. It was observed that truxene derivatives with carbonyl moiety exhibited faster decay than other derivatives. Benzyl groups play some role in the excited state dynamics as decay becomes slower when the spiro moiety was replaced by benzyl group at C5, C10, and C15 positions. Additionally, we noticed the highest quantum yield in t-butanol solvent and least in acetonitrile.
Acceptor or donor (diaryl B or N)substituted octupolar truxene: Synthesis, structure, and charge-transfer-enhanced fluorescence
Yuan, Mao-Sen,Fang, Qi,Liu, Zhi-Qiang,Guo, Jian-Ping,Chen, Hong-Yu,Yu, Wen-Tao,Xue, Gang,Liu, Dian-Sheng
, p. 7858 - 7861 (2006)
(Graph Presented) Two diaryl B- and N-substituted truxene charge-transfer compounds B3 and N3 have been synthesized. The fluorescence intensities of several nonfunctionalized truxene compounds are 1 order of magnitude weaker than that of B3 and N3. To reveal the structure-property correlations, the X-ray structures of B3 and N3 and their precursors 3 and 4 have been determined. The extended molecular dimension, the especially shortened B-C bond, and the improved planarity of B3 can serve as direct structural evidence for the charge transfer.
F?rster Energy Transport in Metal-Organic Frameworks Is beyond Step-by-Step Hopping
Zhang, Qiongqiong,Zhang, Cankun,Cao, Lingyun,Wang, Zi,An, Bing,Lin, Zekai,Huang, Ruiyun,Zhang, Zhiming,Wang, Cheng,Lin, Wenbin
, p. 5308 - 5315 (2016)
Metal-organic frameworks (MOFs) with light-harvesting building blocks designed to mimic photosynthetic chromophore arrays in green plants provide an excellent platform to study exciton transport in networks with well-defined structures. A step-by-step exciton random hopping model made of the elementary steps of energy transfer between only the nearest neighbors is usually used to describe the transport dynamics. Although such a nearest neighbor approximation is valid in describing the energy transfer of triplet states via the Dexter mechanism, we found it inadequate in evaluating singlet exciton migration that occurs through the F?rster mechanism, which involves one-step jumping over longer distance. We measured migration rates of singlet excitons on two MOFs constructed from truxene-derived ligands and zinc nodes, by monitoring energy transfer from the MOF skeleton to a coumarin probe in the MOF cavity. The diffusivities of the excitons on the frameworks were determined to be 1.8 × 10-2 cm2/s and 2.3 × 10-2 cm2/s, corresponding to migration distances of 43 and 48 nm within their lifetimes, respectively. "Through space" energy-jumping beyond nearest neighbor accounts for up to 67% of the energy transfer rates. This finding presents a new perspective in the design and understanding of highly efficient energy transport networks for singlet excited states.
Cost-effective hole transporting material for stable and efficient perovskite solar cells with fill factors up to 82%
Guan, Lei,Yin, Xinxing,Zhao, Dewei,Wang, Changlei,An, Qiaoshi,Yu, Jiangsheng,Shrestha, Niraj,Grice, Corey R.,Awni, Rasha A.,Yu, Yue,Song, Zhaoning,Zhou, Jie,Meng, Weiwei,Zhang, Fujun,Ellingson, Randy J.,Wang, Jianbo,Tang, Weihua,Yan, Yanfa
, p. 23319 - 23327 (2017)
A new small molecule-based hole selective material (HSM), 4,4′,4′′-(7,7′,7′′-(5,5,10,10,15,15-hexahexyl-10,15-dihydro-5H-diindeno[1,2-a:1′,2′-c]fluorene-2,7,12-triyl)tris(2,3-dihydrothieno[3,4-b][1,4]dioxine-7,5-diyl))tris(N,N-bis(4-methoxyphenyl)aniline) (TRUX-E-T), has been developed by a facile synthesis with reduced cost. The highest occupied molecular orbital energy level and lowest unoccupied molecular orbital energy level of TRUX-E-T are -5.10 and -2.50 eV, respectively, making it a suitable HSM for lead iodide perovskite solar cells. TRUX-E-T can be smoothly deposited onto perovskite layers, enabling efficient perovskite solar cells with thin TRUX-E-T layers (～50 nm), which helps cut the unit cost of the HSL used in PVSCs to approximately one-fortieth (1/40) of 2,2′,7,7′-tetrakis (N,N-di-p-methoxyphenylamino)-9,9′-spirobifluorene (spiro-OMeTAD). Additionally, TRUX-E-T exhibits hole mobilities as high as 2.47 × 10-4 cm2 V-1 s-1, better than spiro-OMeTAD. As a result, our perovskite solar cells using TRUX-E-T have shown high fill factors up to 82%. The champion cell achieved a maximum power conversion efficiency of 18.35% (16.44%) when measured under reverse (forward) voltage scan under AM1.5 G 100 mW cm-2 illumination. Our un-encapsulated cells exhibited good stability in ambient air, maintaining 96.4% of their initial efficiency of 18.35% after 20 days of storage.
Strong Ground- and Excited-State Charge Transfer in C3-Symmetric Truxene-Derived Phenothiazine-Tetracyanobutadine and Expanded Conjugates
Sharma, Rekha,Thomas, Michael B.,Misra, Rajneesh,D'Souza, Francis
, p. 4350 - 4355 (2019)
The C3-symmetric star-shaped phenothiazene-substituted truxene 1 was reacted with the electron acceptors tetracyanoethylene (TCNE) and 7,7,8,8-tetracyanoquinodimethane (TCNQ). The cycloaddition–retroelectrocyclization reaction yields the conjugates 2 and 3. A combination of spectral, electrochemical, and photophysical investigations of 2 and 3 reveals that the functionalization of the triple bond has a pronounced effect on their ground and excited-state interactions. Specifically, the existence of strong ground-state interactions between phenothiazine and the electron-accepting groups results in charge-transfer states, while subsequent ultrafast charge separation yields electron transfer products. This is unprecedented not only in phenothiazine chemistry but also in tetracyanobutadiene- and dicyanoquinodimethane-derived donor–acceptor conjugates. Additionally, by manipulating spectroelectrochemical data, a spectrum of the charge-separated species is construed for the first time, and shown to be highly useful in interpreting the rather complex transient spectra.
A Case Study on the Influence of Substitutes on Interlayer Stacking of 2D Covalent Organic Frameworks
Fan, Yu,Wen, Qiang,Zhan, Tian-Guang,Qi, Qiao-Yan,Xu, Jia-Qiang,Zhao, Xin
, p. 5668 - 5672 (2017)
Interlayer stacking of 2D covalent organic frameworks (COFs) plays a crucial role in determining not only the geometry of channels inside COFs but also the mobility of carrier transport between COF layers. However, though topological structures of 2D COFs monolayers can be precisely predicted through the structures of building blocks, factors affecting their interlayer stacking remain poorly understood. In this work, a truxene-based building block on which six methyl groups are introduced was designed. The condensation of it with 1,4-diaminobenzene or benzidine afforded 2D COFs with the methyl groups extending out-of-plane of the layers. A significant influence of the methyl groups on interlayer stacking of the COFs was revealed by the adoption of inclined packing of monolayers, which has never been experimentally observed before. This unprecedented stacking manner was confirmed by powder X-ray diffraction analysis, pore-size distribution analysis, and TEM investigation.
Fusing three perylenebisimide branches and a truxene core into a star-shaped chromophore with strong two-photon excited fluorescence and high photostability
Xie, Yuanpeng,Zhang, Xinfu,Xiao, Yi,Zhang, Youdi,Zhou, Fan,Qi, Jing,Qu, Junle
, p. 4338 - 4340 (2012)
A novel star-shaped chromophore, Tr-PBI, was constructed by fusing three perylenebisimide branches and a truxene core. Tr-PBI exhibits high photostability and excellent two-photon properties: the maximum of δTPA is 11000 GM at 990 nm and fluorescence quantum efficiency Φ is 0.40 in THF. The Royal Society of Chemistry 2012.
Synthesis of new truxene derivatives: Possible precursors of fullerene partial structures?
Dehmlow, Eckehard V.,Kelle, Torsten
, p. 2021 - 2031 (1997)
Preparations of compound 4 and of truxene derivatives 5, 6a,b, 7, 8, 10a,b, 11, 12a,b, and 13a,b are described. These substances are potential starting materials for the synthesis of bowl shaped polyaromatic compounds containing structural elements of fullerenes.
Effective blocking of the molecular aggregation of novel truxene-based emitters with spirobifluorene and electron-donating moieties for furnishing highly efficient non-doped blue-emitting OLEDs
Yao, Chunliang,Yu, Yue,Yang, Xiaolong,Zhang, Huiming,Huang, Zuan,Xu, Xianbin,Zhou, Guijiang,Yue, Ling,Wu, Zhaoxin
, p. 5783 - 5794 (2015)
Several truxene-based blue fluorescent emitters bearing different functional moieties and peripheral spirobifluorene groups have been successfully designed and synthesized. Through tuning the chemical structures and electronic characters of the functional moieties, both optimized molecular configuration and elevated highest occupied molecular orbital (HOMO) energy levels have been afforded to the truxene-based emitters, representing a new effective strategy for solving the problems of molecular aggregation and poor charge carrier injection/transport associated with the truxene-based blue emitters. Owing to the sophisticated strategy, the concerned emitters can furnish highly efficient non-doped blue-emitting OLEDs with a maximum current efficiency (ηL) of 7.41 cd A-1, an external quantum efficiency (ηext) of 4.33%, and a power efficiency (ηP) of 6.79 lm W-1, representing the state-of-the-art EL efficiencies ever achieved by the truxene-based blue emitters. All promising results will not only show the great potential of the concerned truxene-based blue fluorescent emitters in the field of OLEDs, but also furnish valuable clues for developing high-performance truxene-based emitters.
