共查询到20条相似文献,搜索用时 635 毫秒
1.
Dr. Hua Lu Dr. Soji Shimizu Dr. John Mack Prof. Zhen Shen Prof. Nagao Kobayashi 《化学:亚洲杂志》2011,6(4):1026-1037
A series of fused‐ring‐expanded aza‐boradiazaindacene (aza‐BODIPY) dyes have been synthesized by reacting arylmagnesium bromides with phthalonitriles or naphthalenedicarbonitriles. An analysis of the structure–property relationships has been carried out based on X‐ray crystallography, optical spectroscopy, and theoretical calculations. Benzo and 1,2‐naphtho‐fused 3,5‐diaryl aza‐BODIPY dyes display markedly red shifted absorption and emission bands in the near‐IR region (>700 nm) due to changes in the energies of the frontier MOs relative to those of 1,3,5,7‐tetraaryl aza‐BODIPYs. Only one 1,2‐naphtho‐fused aza‐BODIPY of the three possible isomers is formed due to steric effects, and 2,3‐naphtho‐fused compounds could not be characterized because the final BF2 complexes are unstable in solution. The incorporation of a N(CH3)2 group at the para‐positions of a benzo‐fused 3,5‐diaryl aza‐BODIPY quenches the fluorescence in polar solvents and results in a ratiometric pH response, which could be used in future practical applications as an NIR “turn‐on” fluorescence sensor. 相似文献
2.
Synthesis of 3,8‐Dichloro‐6‐ethyl‐1,2,5,7‐tetramethyl–BODIPY from an Asymmetric Dipyrroketone and Reactivity Studies at the 3,5,8‐Positions
下载免费PDF全文
![点击此处可从《Chemistry (Weinheim an der Bergstrasse, Germany)》网站下载免费的PDF全文](/ch/ext_images/free.gif)
Ning Zhao Prof. Dr. M. Graça H. Vicente Dr. Frank R. Fronczek Prof. Dr. Kevin M. Smith 《Chemistry (Weinheim an der Bergstrasse, Germany)》2015,21(16):6181-6192
The asymmetric BODIPY 1 a (BODIPY=4,4‐difluoro‐4‐bora‐3a,4a‐diaza‐s‐indacene), containing two chloro substituents at the 3,8‐positions and a reactive 5‐methyl group, was synthesized from the asymmetric dipyrroketone 3 , which was readily obtained from available pyrrole 2 a . The reactivity of 3,8‐dichloro‐6‐ethyl‐1,2,5,7‐tetramethyl‐BODIPY 1 a was investigated by using four types of reactions. This versatile BODIPY undergoes regioselective Pd0‐catalyzed Stille coupling reactions and/or regioselective nucleophilic addition/elimination reactions, first at the 8‐chloro and then at the 3‐chloro group, using a variety of organostannanes and N‐, O‐, and S‐centered nucleophiles. On the other hand, the more reactive 5‐methyl group undergoes regioselective Knoevenagel condensation with an aryl aldehyde to produce a monostyryl‐BODIPY, and oxidation with 2,3‐dichloro‐5,6‐dicyano‐1,4‐benzoquinone (DDQ) gives the corresponding 5‐formyl‐BODIPY. Investigation of the reactivity of asymmetric BODIPY 1 a led to the preparation of a variety of functionalized BODIPYs with λmax of absorption and emission in the ranges 487–587 and 521–617 nm, respectively. The longest absorbing/emitting compound was the monostyryl‐BODIPY 16 , and the largest Stokes shift (49 nm) and fluorescence quantum yield (0.94) were measured for 5‐thienyl‐8‐phenoxy‐BODIPY 15 . The structural properties (including 16 X‐ray structures) of the new series of BODIPYs were investigated. 相似文献
3.
Synthesis,Structure, and Optical Studies of Donor–Acceptor‐Type Near‐Infrared (NIR) Aza–Boron‐Dipyrromethene (BODIPY) Dyes
下载免费PDF全文
![点击此处可从《化学:亚洲杂志》网站下载免费的PDF全文](/ch/ext_images/free.gif)
Naresh Balsukuri Mohsin Y. Lone Dr. Prakash C. Jha Dr. Shigeki Mori Dr. Iti Gupta 《化学:亚洲杂志》2016,11(10):1572-1587
Six donor–acceptor‐type near‐infrared (NIR) aza–boron‐dipyrromethene (BODIPY) dyes and their corresponding aza–dipyrrins were designed and synthesized. The donor moieties at the 1,7‐positions of the aza–BODIPY core were varied from naphthyl to N‐phenylcarbazole to N‐butylcarbazole. The 3,5‐positions were also substituted with phenyl or thienyl groups in the aza–BODIPYs. Photophysical, electrochemical, and computational studies were carried out. The absorption and emission spectra of aza–BODIPYs were significantly redshifted (≈100 nm) relative to the parent tetraphenylaza–BODIPY. Fluorescence studies suggested effective energy transfer (up to 93 %) from donor groups to the aza–BODIPY core in all of the compounds under study. Time‐dependent (TD)‐DFT studies indicated effective electronic interactions between energy donor groups and aza–dipyrrin unit in all the aza–BODIPYs studied. The HOMO–LUMO gap (ΔE) calculated from cyclic voltammetry data was found to be lower for six aza–BODIPYs relative to their corresponding aza–dipyrrins. 相似文献
4.
meso‐Ester and Carboxylic Acid Substituted BODIPYs with Far‐Red and Near‐Infrared Emission for Bioimaging Applications
下载免费PDF全文
![点击此处可从《Chemistry (Weinheim an der Bergstrasse, Germany)》网站下载免费的PDF全文](/ch/ext_images/free.gif)
Yong Ni Prof. Lintao Zeng Dr. Nam‐Young Kang Prof. Kuo‐Wei Huang Prof. Liang Wang Zebing Zeng Prof. Young‐Tae Chang Prof. Jishan Wu 《Chemistry (Weinheim an der Bergstrasse, Germany)》2014,20(8):2301-2310
A series of meso‐ester‐substituted BODIPY derivatives 1–6 are synthesized and characterized. In particular, dyes functionalized with oligo(ethylene glycol) ether styryl or naphthalene vinylene groups at the α positions of the BODIPY core ( 3 – 6 ) become partially soluble in water, and their absorptions and emissions are located in the far‐red or near‐infrared region. Three synthetic approaches are attempted to access the meso‐carboxylic acid (COOH)‐substituted BODIPYs 7 and 8 from the meso‐ester‐substituted BODIPYs. Two feasible synthetic routes are developed successfully, including one short route with only three steps. The meso‐COOH‐substituted BODIPY 7 is completely soluble in pure water, and its fluorescence maximum reaches around 650 nm with a fluorescence quantum yield of up to 15 %. Time‐dependent density functional theory calculations are conducted to understand the structure–optical properties relationship, and it is revealed that the Stokes shift is dependent mainly on the geometric change from the ground state to the first excited singlet state. Furthermore, cell staining tests demonstrate that the meso‐ester‐substituted BODIPYs ( 1 and 3 – 6 ) and one of the meso‐COOH‐substituted BODIPYs ( 8 ) are very membrane‐permeable. These features make these meso‐ester‐ and meso‐COOH‐substituted BODIPY dyes attractive for bioimaging and biolabeling applications in living cells. 相似文献
5.
Dr. Hua Lu Qiuhong Wang Lizhi Gai Prof. Zhifang Li Yuan Deng Dr. Xuqiong Xiao Prof. Guoqiao Lai Prof. Zhen Shen 《Chemistry (Weinheim an der Bergstrasse, Germany)》2012,18(25):7852-7861
Boron dipyrromethenes (BODIPYs) with bulky triphenylsilylphenyl(ethynyl) and triphenylsilylphenyl substituents on pyrrole sites were prepared via Hagihara–Sonogashira and Suzuki–Miyaura cross‐coupling with ethynyl‐terminated tetraphenylsilane and boronic acid‐terminated tetraphenylsilane. The chromophores are designed to prevent intermolecular π–π stacking interaction and enhance fluorescence in the solid state. Single crystals of 1 a and 2 b for X‐ray structural analysis were obtained, and weak π–π stacking interactions of the neighboring BODIPY molecules were observed. Spectroscopic properties of all of the dyes in various solvents and in films were investigated. Triphenylsilylphenyl‐substituted BODIPYs generally show more pronounced increases in solid‐state emission than triphenylsilylphenyl(ethynyl)‐substituted BODIPYs. Although the simple BODIPYs do not exhibit any fluorescence in the solid state (Φ=0), arylsilyl‐substituted BODIPYs exhibit weak to moderate solid‐state fluorescence with quantum yields of 0.03, 0.07, 0.10, and 0.25. The structure–property relationships were analyzed on the basis of X‐ray crystallography, optical spectroscopy, cyclic voltammetry, and theoretical calculations. 相似文献
6.
Acidic Condensation of BODIPYs with Aldehydes: A Quick and Versatile Route to Alkenyl‐BODIPYs and C(sp3)‐Connected DYEmers
下载免费PDF全文
![点击此处可从《Chemistry (Weinheim an der Bergstrasse, Germany)》网站下载免费的PDF全文](/ch/ext_images/free.gif)
Dr. Johannes Ahrens Dr. Birte Cordes Dr. Richard Wicht Dr. Benedikt Wolfram Prof. Dr. Martin Bröring 《Chemistry (Weinheim an der Bergstrasse, Germany)》2016,22(30):10320-10325
The condensation of aldehydes with BODIPY (boron dipyrrin) luminophores was investigated. Formaldehyde can be used to connect two BODIPYs at each of the three pyrrolic C positions (α‐, β‐, and β′‐positions) in a quick and highly selective manner, yielding new DYEmers (di‐ and oligomeric BODIPY derivatives) with varied photophysical properties. Benzaldehydes form DYEmers only at the β‐ and the β′‐positions. For aliphatic aldehydes the DYEmer formation competes with the elimination of water from a proposed alcohol intermediate, leading to the formation of α‐ and β‐alkenyl‐BODIPYs. 2‐Phenylacetaldehyde and similar precursors exclusively yield elimination products. These acid‐mediated transformations are valuable alternatives to the well‐established, base‐promoted Knoevenagel condensation protocol that is typically employed in the preparation of BODIPYs with near infrared (NIR)‐shifted absorptions. 相似文献
7.
Yan‐Wei Wang Ana B. Descalzo Dr. Zhen Shen Prof. Xiao‐Zeng You Prof. Knut Rurack Dr. 《Chemistry (Weinheim an der Bergstrasse, Germany)》2010,16(9):2887-2903
A new series of boron–dipyrromethene (BDP, BODIPY) dyes with dihydronaphthalene units fused to the β‐pyrrole positions ( 1 a – d , 2 ) has been synthesised and spectroscopically investigated. All the dyes, except pH‐responsive 1 d in polar solvents, display intense emission between 550–700 nm. Compounds 1 a and 1 b with a hydrogen atom and a methyl group in the meso position of the BODIPY core show spectroscopic properties that are similar to those of rhodamine 101, thus rendering them potent alternatives to the positively charged rhodamine dyes as stains and labels for less polar environments or for the dyeing of latex beads. Compound 1 d , which carries an electron‐donating 4‐(dimethylamino)phenyl group in the meso position, shows dual fluorescence in solvents more polar than dibutyl ether and can act as a pH‐responsive “light‐up” probe for acidic pH. Correlation of the pKa data of 1 d and several other meso‐(4‐dimethylanilino)‐substituted BODIPY derivatives allowed us to draw conclusions on the influence of steric crowding at the meso position on the acidity of the aniline nitrogen atom. Preparation and investigation of 2 , which carries a nitrogen instead of a carbon as the meso‐bridgehead atom, suggests that the rules of colour tuning of BODIPYs as established so far have to be reassessed; for all the reported couples of meso‐C‐ and meso‐N‐substituted BODIPYs, the exchange leads to pronounced redshifts of the spectra and reduced fluorescence quantum yields. For 2 , when compared with 1 a , the opposite is found: negligible spectral shifts and enhanced fluorescence. Additional X‐ray crystallographic analysis of 1 a and quantum chemical modelling of the title and related compounds employing density functional theory granted further insight into the features of such sterically crowded chromophores. 相似文献
8.
Lei Chen Dandan Chen Yifei Jiang Jicheng Zhang Jiangbo Yu Christopher C. DuFort Sunil R. Hingorani Xuanjun Zhang Changfeng Wu Daniel T. Chiu 《Angewandte Chemie (Weinheim an der Bergstrasse, Germany)》2019,131(21):7082-7086
Bright long‐wavelength‐excitable semiconducting polymer dots (LWE‐Pdots) are highly desirable for in vivo imaging and multiplexed in vitro bioassays. LWE‐Pdots have been obtained by incorporating a near‐infrared (NIR) emitter into the backbone of a polymer host to develop a binary donor–acceptor (D–A) system. However, they usually suffer from severe concentration quenching and a trade‐off between fluorescence quantum yield (Φf) and absorption cross‐section (σ). Herein, we describe a ternary component (D1/D2–A) strategy to achieve ultrabright, green laser‐excitable Pdots with narrow‐band NIR emission by introducing a BODIPY‐based assistant polymer donor as D1. The D1/D2–A Pdots possess improved Φf and σ compared to corresponding binary D2–A Pdots. Their Φf is as high as 40.2 %, one of the most efficient NIR Pdots reported. The D1/D2–A Pdots show ultrahigh single‐particle brightness, 83‐fold brighter than Qdot 705 when excited by a 532 nm laser. When injected into mice, higher contrast in vivo tumor imaging was achieved using the ternary Pdots versus the binary D–A Pdots. 相似文献
9.
Timsy Uppal Dr. Xiaoke Hu Dr. Frank R. Fronczek Stephanie Maschek Prof. Petia Bobadova‐Parvanova Prof. M. Graça H. Vicente 《Chemistry (Weinheim an der Bergstrasse, Germany)》2012,18(13):3893-3905
A series of new functionalized mono‐ and dibenzo‐appended BODIPY dyes were synthesized from a common tetrahydroisoindole precursor following two different synthetic routes. Route A involved the assembly of the BODIPY core prior to aromatization, while in Route B the aromatization step was performed first. In general, Route A gave higher yields of the target dibenzo‐BODIPYs, due to the ease of aromatization of the BODIPYs compared with the corresponding dipyrromethenes, probably due to their higher stability under the oxidative conditions (2,3‐dichloro‐5,6‐dicyano‐1,4‐benzoquinone in refluxing toluene). However, due to the slow oxidation of highly electron‐deficient BODIPY 3 c bearing a meso‐C6F5 group, dibenzo‐BODIPY 4 c was obtained, in 35 % overall from dipyrromethane, only by Route B. Computational calculations performed at the 6‐31G(d,p) level are in agreement with the experimental results, showing similar relative energies for all reaction intermediates in both routes. In addition, BODIPY 3 c had the highest molecular electrostatic potential (MEPN), confirming its high electron deficiency and consequent resistance toward oxidation. X‐ray analyses of eight BODIPYs and several intermediates show that benzannulation further enhances the planarity of these systems. The π‐extended BODIPYs show strong red‐shifted absorptions and emissions, about 50–60 nm per benzoannulated ring, at 589–658 and 596–680 nm, respectively. In particular, db‐BODIPY 4 c bearing a meso‐C6F5 group showed the longest λmax of absorption and emission, along with the lowest fluorescence quantum yield (0.31 in CH2Cl2); on the other hand monobenzo‐BODIPY 8 showed the highest quantum yield (0.99) of this series. Cellular investigations using human carcinoma HEp2 cells revealed high plasma membrane permeability for all dibenzo‐BODIPYs, low dark‐ and photo‐cytotoxicities and intracellular localization in the cell endoplasmic reticulum, in addition to other organelles. Our studies indicate that benzo‐appended BODIPYs, in particular the highly stable meso‐substituted BODIPYs, are promising fluorophores for bioimaging applications. 相似文献
10.
Zhang M Hao E Zhou J Yu C Bai G Wang F Jiao L 《Organic & biomolecular chemistry》2012,10(10):2139-2145
Direct oxidative nucleophilic substitution of the 3-hydrogen of BODIPY dyes by pyrrole has been developed under reflux condition under oxygen, from which a series of pyrrolyldipyrrinato BF(2) complexes 1a-h, as extended BODIPYs, have been synthesized. Most of these BODIPYs show strong fluorescence emissions at wavelengths over 600 nm in six solvents of different polarity. Removal of the BF(2) group from BODIPY 1e gave the corresponding free base pyrrolyldipyrrin 7 as an analog of the natural product prodigiosin, in high yield. 相似文献
11.
Alexander L. Antaris Dr. Junlei Chang Dr. Justin Z. Wu Bo Zhang Dr. Kai Cheng Prof. Calvin J. Kuo Prof. Hongjie Dai 《Angewandte Chemie (International ed. in English)》2015,54(49):14758-14762
Compared to imaging in the visible and near‐infrared regions below 900 nm, imaging in the second near‐infrared window (NIR‐II, 1000–1700 nm) is a promising method for deep‐tissue high‐resolution optical imaging in vivo mainly owing to the reduced scattering of photons traversing through biological tissues. Herein, semiconducting single‐walled carbon nanotubes with large diameters were used for in vivo fluorescence imaging in the long‐wavelength NIR region (1500–1700 nm, NIR‐IIb). With this imaging agent, 3–4 μm wide capillary blood vessels at a depth of about 3 mm could be resolved. Meanwhile, the blood‐flow speeds in multiple individual vessels could be mapped simultaneously. Furthermore, NIR‐IIb tumor imaging of a live mouse was explored. NIR‐IIb imaging can be generalized to a wide range of fluorophores emitting at up to 1700 nm for high‐performance in vivo optical imaging. 相似文献
12.
Synthesis of π-expanded BODIPYs and their fluorescent properties in the visible-near-infrared region
Tetsuo Okujima Yuya Tomimori Jun Nakamura Hiroko Yamada Hidemitsu Uno Noboru Ono 《Tetrahedron》2010,66(34):6895-7270
A series of π-expanded boron-dipyrromethenes (BODIPYs) fused with aromatic rings at β,β-positions, such as benzene, acenaphthylene, and benzofluoranthene were prepared by the reaction of BF3·OEt2 with bicyclo[2.2.2]octadiene-fused dipyrromethene and the subsequent retro Diels-Alder reaction. These BODIPYs exhibited the absorptions and the fluorescence emissions over wide range of visible-near-infrared region at 500-800 nm. BODIPYs composed of two fluorantho[8,9-f]isoindoles absorbed and emitted at red-region over 750 nm with absolute fluorescence quantum yield (Φf) of ca. 0.3, although they are unstable under air in room light. BODIPY composed fluorantho[8,9-f]isoindole and acenaphtho[1,2-c]pyrrole was stable and showed a bright fluorescence emission at 695 nm with high Φf of 0.70. 相似文献
13.
Soonchul Kang Hironobu Hayashi Tomokazu Umeyama Dr. Yoshihiro Matano Prof. Nikolai V. Tkachenko Prof. Helge Lemmetyinen Prof. Hiroshi Imahori Prof. 《化学:亚洲杂志》2008,3(12):2065-2074
Trifluoroacetic acid‐catalyzed condensation of pyrrole with electron‐deficient and sterically hindered 3,5‐bis(trifluoromethyl)benzaldehyde results in the unexpected production of a series of meso‐3,5‐bis(trifluoromethyl)phenyl‐substituted expanded porphyrins including [22]sapphyrin 2 , N‐fused [22]pentaphyrin 3 , [26]hexaphyrin 4 , and intact [32]heptaphyrin 5 together with the conventional 5,10,15,20‐tetrakis(3,5‐bis(trifluoromethyl)phenyl)porphyrin 1 . These expanded porphyrins are characterized by mass spectrometry, 1H NMR spectroscopy, UV/Vis/NIR absorption spectroscopy, and fluorescence spectroscopy. The optical and electrochemical measurements reveal a decrease in the HOMO–LUMO gap with increasing size of the conjugated macrocycles, and in accordance with the trend, the deactivation of the excited singlet state to the ground state is enhanced. 相似文献
14.
Synthesis and Characterization of Far‐Red/NIR‐Fluorescent BODIPY Dyes,Solid‐State Fluorescence,and Application as Fluorescent Tags Attached to Carbon Nano‐onions
下载免费PDF全文
![点击此处可从《Chemistry (Weinheim an der Bergstrasse, Germany)》网站下载免费的PDF全文](/ch/ext_images/free.gif)
Dr. Juergen Bartelmess Dr. Michele Baldrighi Dr. Valentina Nardone Dr. Emilio Parisini David Buck Prof. Dr. Luis Echegoyen Prof. Dr. Silvia Giordani 《Chemistry (Weinheim an der Bergstrasse, Germany)》2015,21(27):9727-9732
A series of π‐extended distyryl‐substituted boron dipyrromethene (BODIPY) derivatives with intense far‐red/near‐infrared (NIR) fluorescence was synthesized and characterized, with a view to enhance the dye’s performance for fluorescence labeling. An enhanced brightness was achieved by the introduction of two methyl substituents in the meso positions on the phenyl group of the BODIPY molecule; these substituents resulted in increased structural rigidity. Solid‐state fluorescence was observed for one of the distyryl‐substituted BODIPY derivatives. The introduction of a terminal bromo substituent allows for the subsequent immobilization of the BODIPY fluorophore on the surface of carbon nano‐onions (CNOs), which leads to potential imaging agents for biological and biomedical applications. The far‐red/NIR‐fluorescent CNO nanoparticles were characterized by absorption, fluorescence, and Raman spectroscopies, as well as by thermogravimetric analysis, dynamic light scattering, high‐resolution transmission electron microscopy, and confocal microscopy. 相似文献
15.
A novel 3,4,4a-trihydroxanthene-fused pyrrole 2 was synthesized by the reaction of 2,3,4,4a-tetrahydro-1H-xanthen-1-one with 3-phenyl-2H-azirine in the presence of LDA. Utilizing this pyrrole 2, a NIR BODIPY 1 (λ(abs) = 732 nm, λ(em) = 747 nm) has been prepared. The new BODIPY 1 was stable, non-cytotoxic, and suited to labeling living cells for imaging assay in the NIR region. 相似文献
16.
《化学:亚洲杂志》2017,12(5):561-567
We describe herein the first synthesis of silyl‐ and disilanyl‐BODIPYs through transition‐metal‐catalyzed dehalosilylation of iodo‐BODIPYs using a Pd(P(t Bu)3)2/Et3N/toluene system. Various mono‐ and bis‐silyl‐BODIPYs, mono‐ and bis‐disilanyl‐BODIPYs and bis‐BODIPYs linked by silylene and SiOSi groups were synthesized by using this straightforward method. Silyl‐ and disilanyl‐substitution significantly modifies the spectroscopic properties of the BODIPY, in which the fluorescence quantum yields of the silyl‐BODIPYs are remarkably increased, whereas the emission spectra of disilanyl‐BODIPYs are red‐shifted due to effective σ(SiSi)–π(BODIPY) conjugation. 相似文献
17.
Rational Design of Emissive NIR‐Absorbing Chromophores: RhIII Porphyrin‐Aza‐BODIPY Conjugates with Orthogonal Metal–Carbon Bonds
下载免费PDF全文
![点击此处可从《Chemistry (Weinheim an der Bergstrasse, Germany)》网站下载免费的PDF全文](/ch/ext_images/free.gif)
Jinfeng Zhou Lizhi Gai Dr. Zhikuan Zhou Wu Yang Dr. John Mack Kejing Xu Prof. Jianzhang Zhao Dr. Yue Zhao Dr. Hailin Qiu Prof. Kin Shing Chan Prof. Zhen Shen 《Chemistry (Weinheim an der Bergstrasse, Germany)》2016,22(37):13201-13209
The facile synthesis of Group 9 RhIII porphyrin‐aza‐BODIPY conjugates that are linked through an orthogonal Rh?C(aryl) bond is reported. The conjugates combine the advantages of the near‐IR (NIR) absorption and intense fluorescence of aza‐BODIPY dyes with the long‐lived triplet states of transition metal rhodium porphyrins. Only one emission peak centered at about 720 nm is observed, irrespective of the excitation wavelength, demonstrating that the conjugates act as unique molecules rather than as dyads. The generation of a locally excited (LE) state with intramolecular charge‐transfer (ICT) character has been demonstrated by solvatochromic effects in the photophysical properties, singlet oxygen quantum yields in polar solvents, and by the results of density functional theory (DFT) calculations. In nonpolar solvents, the RhIII conjugates exhibit strong aza‐BODIPY‐centered fluorescence at around 720 nm (ΦF=17–34 %), and negligible singlet oxygen generation. In polar solvents, enhancements of the singlet‐oxygen quantum yield (ΦΔ=19–27 %, λex=690 nm) have been observed. Nanosecond pulsed time‐resolved absorption spectroscopy confirms that relatively long‐lived triplet excited states are formed. The synthetic methodology outlined herein provides a useful strategy for the assembly of functional materials that are highly desirable for a wide range of applications in material science and biomedical fields. 相似文献
18.
Van‐Nghia Nguyen Yubin Yim Sangin Kim Bokyeong Ryu K. M. K. Swamy Gyoungmi Kim Nahyun Kwon C‐Yoon Kim Sungnam Park Juyoung Yoon 《Angewandte Chemie (International ed. in English)》2020,59(23):8957-8962
Novel BODIPY photosensitizers were developed for imaging‐guided photodynamic therapy. The introduction of a strong electron donor to the BODIPY core through a phenyl linker combined with the twisted arrangement between the donor and the BODIPY acceptor is essential for reducing the energy gap between the lowest singlet excited state and the lowest triplet state (ΔEST), leading to a significant enhancement in the intersystem crossing (ISC) of the BODIPYs. Remarkably, the BDP‐5 with the smallest ΔEST (ca. 0.44 eV) exhibited excellent singlet oxygen generation capabilities in both organic and aqueous solutions. BDP‐5 also displayed bright emission in the far‐red/near‐infrared region in the condensed states. More importantly, both in vitro and in vivo studies demonstrated that BDP‐5 NPs displayed a high potential for photodynamic cancer therapy and bioimaging. 相似文献
19.
Near‐Infrared‐Emitting BODIPY‐trisDOTA111In as a Monomolecular Multifunctional Imaging Probe: From Synthesis to In Vivo Investigations
下载免费PDF全文
![点击此处可从《Chemistry (Weinheim an der Bergstrasse, Germany)》网站下载免费的PDF全文](/ch/ext_images/free.gif)
Dr. Claire Bernhard Dr. Damien Lhenry Dr. Mathieu Moreau Dr. Sabin Carme Dr. Alexandra Oudot Dr. Bertrand Collin Dr. Jean‐Marc Vrigneaud Dr. Peggy Provent Prof. François Brunotte Prof. Franck Denat Dr. Christine Goze 《Chemistry (Weinheim an der Bergstrasse, Germany)》2016,22(36):12670-12674
A new generation of monomolecular imaging probes (MOMIP) based on a distyryl‐BODIPY (BODIPY=boron‐dipyrromethene) coupled with three DOTA macrocycles has been prepared (DOTA=1,4,7,10‐tetraazacyclododecane‐1,4,7,10‐tetraacetic acid). The MOMIP presents good fluorescence properties and is very stable in serum. The bimodal probe was conjugated to trastuzumab, and an optical in vivo study showed high accumulation of the imaging agent at the tumor site. 111In radiometallation of the bioconjugate was performed in high radiochemical yield, highlighting the potential of this new BODIPY‐chelators derivative as a bimodal imaging probe. 相似文献
20.
DMAP‐BODIPY Alkynes: A Convenient Tool for Labeling Biomolecules for Bimodal PET–Optical Imaging
下载免费PDF全文
![点击此处可从《Chemistry (Weinheim an der Bergstrasse, Germany)》网站下载免费的PDF全文](/ch/ext_images/free.gif)
Dr. Bertrand Brizet Dr. Victor Goncalves Dr. Claire Bernhard Prof. Pierre D. Harvey Prof. Franck Denat Dr. Christine Goze 《Chemistry (Weinheim an der Bergstrasse, Germany)》2014,20(40):12933-12944
Several new boron dipyrromethene/N,N‐dimethylaminopyridine (BODIPY‐DMAP) assemblies were synthesized as precursors for bimodal imaging probes (optical imaging, OI/positron emission tomography, PET). The photophysical properties of the new compounds were also studied. The first proof‐of‐concept was obtained with the preparation of several new BODIPY‐labeled bombesins and evaluation of the affinity for bombesin receptors by using a competition binding assay. Fluorination reactions were investigated on DMAP‐BODIPY precursors as well as on DMAP‐BODIPY‐labeled bombesins. Chemical modifications on the BODIPY core were also performed to obtain luminescent dyes emitting in the therapeutic window (650–900 nm), suitable for in vivo imaging, making these compounds promising precursors for PET/optical dual‐modality imaging agents. 相似文献