- Fluorescence Colour Control in Perylene-Labeled Polymer Chains Trapped by Nanotextured Silicon
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The ability to modulate, tune, and control fluorescence colour has attracted much attention in photonics-related research fields. Thus far, it has been impossible to achieve fluorescence colour control (FCC) for material with a fixed structure, size, surrounding medium, and concentration. Here, we propose a novel approach to FCC using optical tweezers. We demonstrate an optical trapping technique using nanotextured Si (black-Si) that can efficiently trap polymer chains. By increasing the laser intensity, the local concentration of perylene-labelled water-soluble polymer chains increased inside the trapping potential. Accordingly, the excimer fluorescence of perylene increased while the monomer fluorescence decreased, evidenced by a fluorescence colour change from blue to orange. Using nanostructure-assisted optical tweezing, we demonstrate control of the relative intensity ratio of fluorescence of the two fluorophores, thus showing remote and reversible FCC of the polymer assembly.
- Ivanova, Elena,Juodkazis, Saulius,Kusano, Hazuki,Linklater, Denver P.,Shoji, Tatsuya,Takao, Ryota,Tsuboi, Yasuyuki,Ushiro, Kenta,Yuyama, Ken-ichi
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supporting information
(2022/02/01)
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- PHOTOLYTIC COMPOUNDS AND TRIPLET-TRIPLET ANNIHILATION MEDIATED PHOTOLYSIS
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The invention provides novel photolytic compounds and prodrugs, nanoparticles and compositions thereof, and methods of conducting photolysis mediated by triplet-triplet annihilation.
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Paragraph 0026
(2021/04/17)
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- Fluorescence upconversion by triplet-triplet annihilation in all-organic poly(methacrylate)-terpolymers
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Fluorescence upconversion by triplet-triplet annihilation is demonstrated for a fully polymer-integrated material, i.e. in the limit of restricted diffusion. Organic sensitizer and acceptor are covalently attached to a poly(methacrylate) backbone, yielding a metal-free macromolecular all-in-one system for fluorescence upconversion. Due to the spatial confinement of the optically active molecular components, i.e. annihilator and sensitizer, UC by TTA in the constrained polymer system in solution is achieved at exceptionally low averaged annihilator concentrations. However, the UC quantum yield in the investigated systems is found to be low, highlighting that only chromophores in specific local surroundings yield upconversion in the limit of restricted diffusion. A photophysical model is proposed taking the heterogeneous local environment within the polymers into account.
- Bocklitz, Thomas,Dietzek, Benjamin,G?rls, Helmar,Hager, Martin D.,Schmidt, Benny,Sittig, Maria,W?chtler, Maria,Zechel, Stefan
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p. 4072 - 4079
(2020/03/04)
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- BORON-CONTAINING CYCLIC EMISSIVE COMPOUNDS AND COLOR CONVERSION FILM CONTAINING THE SAME
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The present disclosure relates to novel photoluminescent complexes comprising a BODIPY moiety covalently bonded to a blue light absorbing moiety, a color conversion film comprising the photoluminescent complex, and a back-light unit using the same.
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Page/Page column 60; 61
(2020/10/21)
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- Organic photoredox catalyst with substrate-capture ability: A perylene derivative bearing urethane moiety for reductive coupling of ketones and aldehydes under visible light
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A perylene derivative bearing a urethane moiety served as an efficient photoredox catalyst for the reductive coupling of ketones and aldehydes under visible light, implicating that the urethane moiety captured substrates through hydrogen bonds to lower the LUMO levels of the captured substrates, thus promoting single electron transfer from the reductant anion radical of the perylene moiety to the substrates.
- Okamoto, Shusuke,Tsujioka, Hiroki,Sudo, Atsushi
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supporting information
p. 369 - 372
(2018/03/05)
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- Energy down converting organic fluorophore functionalized mesoporous silica hybrids for monolith-coated light emitting diodes
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The covalent attachment of organic fluorophores in mesoporous silica matrices for usage as energy down converting phosphors without employing inorganic transition or rare earth metals is reported in this article. Triethoxysilylpropyl-substituted derivatives of the blue emitting perylene, green emitting benzofurazane, and red emitting Nile red were synthesized and applied in the synthesis of mesoporous hybrid materials by postsynthetic grafting to commercially available MCM-41. These individually dye-functionalized hybrid materials are mixed in variable ratios to furnish a powder capable of emitting white light with CIE chromaticity coordinates of x = 0.33, y = 0.33 and an external quantum yield of 4.6% upon irradiation at 410 nm. Furthermore, as a proof of concept two different device setups of commercially available UV light emitting diodes, are coated with silica monoliths containing the three triethoxysilylpropyl-substituted fluorophore derivatives. These coatings are able to convert the emitted UV light into light with correlated color temperatures of very cold white (41100 K, 10700 K) as well as a greenish white emission with correlated color temperatures of about 5500 K.
- B?rgardts, Markus,Müller, Thomas J. J.
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supporting information
p. 768 - 778
(2017/06/20)
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- Thiol-Activatable Triplet-Triplet Annihilation Upconversion with Maleimide-Perylene as the Caged Triplet Acceptor/Emitter
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Efficient thiol-activated triplet-triplet annihilation (TTA) upconversion system was devised with maleimide-caged perylene (Py-M) as the thiol-activatable triplet acceptor/emitter and with diiodoBodipy as the triplet photosensitizer. The photophysical processes were studied with steady-state UV-vis absorption spectroscopy, fluorescence spectroscopy, electrochemical properties, and nanosecond transient absorption spectroscopy. The triplet acceptor/emitter Py-M shows week fluorescence (φF = 0.8%), and no upconversion (φUC = 0%) was observed. The quenching of fluorescence of Py-M is due to photoinduced electron-transfer (PET) process from perylene to maleimide-caging unit, which quenches the singlet excited state of perylene. The fluorescence of Py-M was enhanced by 200-fold (φF = 97%) upon addition of thiols such as 2-mercaptoethanol, and the φUC was increased to 5.9%. The unique feature of this thiol-activated TTA upconversion is that the activation is based on addition reaction of the thiols with the caged acceptor/emitter, and no side products were formed. The previously reported cleavage approach gives side products which are detrimental to the TTA upconversion. With nanosecond transient absorption spectroscopy, we found that the triplet excited state of Py-M was not quenched by any PET process, which is different from singlet excited state (fluorescence) of Py-M. The results are useful for study of the triplet excited states of organic chromophores and for activatable TTA upconversion.
- Mahmood, Zafar,Zhao, Jianzhang
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p. 587 - 594
(2016/01/27)
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- Perylen-3-ylmethyl: Fluorescent photoremovable protecting group (FPRPG) for carboxylic acids and alcohols
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Perylen-3-ylmethyl demonstrated as a new fluorescent photoremovable protecting group (FPRPG) for carboxylic acids and alcohols. Carboxylic acids including amino acids were protected as their corresponding esters by coupling with FPRPG, perylen-3-ylmethyl. Photophysical studies of caged esters showed that they all exhibited strong fluorescence properties and their fluorescence quantum yields were in the range of 0.85-0.95. Irradiation of the caged esters using visible light (≥410 nm) in aqueous acetonitrile released the corresponding carboxylic acids in high chemical (94-97%) and quantum (0.072-0.093) yields. The results obtained from the photolysis of the caged ester in different solvents indicated that solvent has influence on the rate of photorelease. Further, we also explored the ability of FPRPG, perylen-3-ylmethyl for the protection of alcohols and phenols.
- Jana, Avijit,Ikbal, Mohammed,Singh, N.D. Pradeep
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supporting information; scheme or table
p. 1128 - 1136
(2012/02/16)
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- Highly efficient and directional homo-and heterodimeric energy transfer materials based on fluorescently derivatized α,γ(γ)-cyclic octapeptides
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Cyclic octapeptides composed of α-amino acids alternated with cis-3-aminocycloalkanecarboxylic acids, self-assemble as drumlike dimers through β-sheet-like, backbone-to-backbone hydrogen bonding. Heterodimerization appears to be significantly more favored
- Brea, Roberto J.,Perez-Alvite, Maria Jesas,Panciera, Michele,Mosquera, Manuel,Castedo, Luis,Granja, Juan R.
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experimental part
p. 110 - 121
(2011/10/08)
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- Molecular implementation of sequential and reversible logic through photochromic energy transfer switching
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Photochromic spiropyrans modified with fluorophores were investigated as molecular platforms for the achievement of fluorescence switching through modulation of energy transfer. The dyads were designed in such a way that energy transfer is only observed for the open forms of the photochrome (merocyanine and protonated merocyanine), whereas the closed spiropyran is inactive as an energy acceptor. This was made possible through a deliberate choice of fluorophores (4-amino-1,8-naphthalimide, dansyl, and perylene) that produce zero spectral overlap with the spiro form and considerable overlap for the merocyanine forms. From the Foerster theory, energy transfer is predicted to be highly efficient and in some cases of 100 % efficiency. The combined switching by photonic (light of I>530 nm) and chemical (base) inputs enabled the creation of a sequential logic device, which is the basic element of a keypad lock. Furthermore, in combination with an anthracene-based acidochromic fluorescence switch, a reversible logic device was designed. This enables the unambiguous coding of different input combinations through multicolour fluorescence signalling. All devices can be conveniently reset to their initial states and repeatedly cycled. Copyright
- Remon, Patricia,Hammarson, Martin,Li, Shiming,Kahnt, Axel,Pischel, Uwe,Andreasson, Joakim
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supporting information; scheme or table
p. 6492 - 6500
(2011/08/06)
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- Pyrenylmethyldeoxyadenosine: A 3′-cap for universal DNA hybridization probes
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A ligand that stabilizes a three-dimensional structure can be expected to have a positive effect on the specificity with which this structure is formed. Here we report on a ligand covalently linked to an oligonucleotide that increases duplex stability, but decreases base-pairing selectivity at the terminus. The ligand consists of a dangling 2′-deoxyadenosine residue with a pyrenylmethyl substituent at the N6-position, that is, a deoxynucleoside with a covalently linked polycyclic aromatic hydrocarbon (PAH). In the presence of the pyrene-bearing nucleosides the UV melting point (ΔTm) of duplexes increases by up to 29.1°C. The modified residue lowers the base-pairing fidelity at the terminal and penultimate position of duplexes with a depression in ΔΔTm observable in 20 out of 24 sequence contexts tested. The effect can be rationalized based on a modeled three-dimensional structure. The results are significant for the understanding of base-pairing fidelity in DNA duplexes as modulated by the presence of a polycyclic aromatic hydrocarbon. The fidelity-decreasing effect may be useful for universal hybridization probes that bind to a broader range of sequences than conventional oligonucleotides.
- Printz, Michael,Richert, Clemens
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experimental part
p. 3390 - 3402
(2010/01/19)
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- Synthesis, spectroscopic, and electrochemical properties of three tetrathiafulvalenes attached to perylene
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Three donor-acceptor dyads 1-3 comprising of a tetrathiafulvalene (TTF) unit linked with perylene by a simple σ-bond were synthesized and characterized. Spectroscopy and cyclic voltammetry provided an indication that intramolecular charge-transfer interactions in their ground states between TTF and perylene for dyads 1-3 are negligible. Compared with the compound perylene, dyads 1-3 exhibited large fluorescence quenching, which might be ascribed to photo-induced electron transfer interaction between TTF and perylene units in the excited state.
- Qiu, Haixiao,Wang, Chengyun,Xu, Jinfeng,Lai, Guoqiao,Shen, Yongjia
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experimental part
p. 1357 - 1362
(2009/12/05)
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- Assembly and exchange of resorcinarene capsules monitored by fluorescence resonance energy transfer
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Resorcinarenes were functionalized with fluorophores and fluorescence resonance energy transfer (FRET) was employed as a tool to probe the dynamic behavior of hydrogen-bonded hexameric assemblies at nanomolar concentrations. The encapsulation of a fluorescent guest inside the capsule made it possible to observe FRET across the mechanical boundary of the hexameric assembly. Copyright
- Barrett, Elizabeth S.,Dale, Trevor J.,Rebek Jr., Julius
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p. 3818 - 3819
(2008/02/03)
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- 5-Alkynyl-2′-deoxyuridines, containing bulky aryl groups: Evaluation of structure-anti-HSV-1 activity relationship
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Four 5-alkynyl-2′-deoxyuridines containing different bulky substituents and flexible linkers between the triple bond and the aromatic residue have been prepared and tested against HSV-1 in Vero cells. Two nucleosides containing carbonyl groups, 5-(4-benzo
- Skorobogatyi, Mikhail V.,Pchelintseva, Anna A.,Petrunina, Anna L.,Stepanova, Irina A.,Andronova, Valeriya L.,Galegov, Georgi A.,Malakhov, Andrei D.,Korshun, Vladimir A.
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p. 1279 - 1287
(2007/10/03)
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- Synthesis of new bifluorophoric probes adapted to studies of donor-donor electronic energy transfer in lipid systems
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A series of bifluorophoric fluorescent probes with identical pairs of chromophores have been synthesized. The fluorophores are 9-anthryl, 3-perylenyl and rhodamine 101, and they are separated by a long rigid (bisteroid) or flexible (dotriacontane) diol sp
- Grechishnikova, Irina V.,Johansson, Lennart B.-A,Molotkovsky, Julian G.
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