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Search for "fluorescence properties" in Full Text gives 59 result(s) in Beilstein Journal of Organic Chemistry.

The Groebke–Blackburn–Bienaymé reaction in its maturity: innovation and improvements since its 21st birthday (2019–2023)

  • Cristina Martini,
  • Muhammad Idham Darussalam Mardjan and
  • Andrea Basso

Beilstein J. Org. Chem. 2024, 20, 1839–1879, doi:10.3762/bjoc.20.162

Graphical Abstract
  • proof of concept, one of the GBB adducts was transformed into a N,C-palladacycle and was investigated as a potential catalyst for carbon–carbon bond-forming reactions. Furthermore, the authors studied in detail the fluorescence properties of the GBB adducts, that will be discussed in chapter 5. As
  • economy (water was the only byproduct) and thermal stability as well as remarkable fluorescence properties. Multicomponent reaction can be also employed to prepare crystalline porous materials namely covalent organic frameworks (COFs). The structural diversity and functionality of COFs were assembled from
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Published 01 Aug 2024

Synthesis of photo- and ionochromic N-acylated 2-(aminomethylene)benzo[b]thiophene-3(2Н)-ones with a terminal phenanthroline group

  • Vladimir P. Rybalkin,
  • Sofiya Yu. Zmeeva,
  • Lidiya L. Popova,
  • Irina V. Dubonosova,
  • Olga Yu. Karlutova,
  • Oleg P. Demidov,
  • Alexander D. Dubonosov and
  • Vladimir A. Bren

Beilstein J. Org. Chem. 2024, 20, 552–560, doi:10.3762/bjoc.20.47

Graphical Abstract
  • . The reverse reaction 3a–c→2a–c with full restoration of the initial absorption and fluorescence properties was characterized by a high activation barrier and could be accomplished by heating a solution of 3a–c in o-dichlorobenzene at 423 K or by passing dry hydrogen chloride through a solution of 3a–c
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Published 11 Mar 2024

Synthesis of π-conjugated polycyclic compounds by late-stage extrusion of chalcogen fragments

  • Aissam Okba,
  • Pablo Simón Marqués,
  • Kyohei Matsuo,
  • Naoki Aratani,
  • Hiroko Yamada,
  • Gwénaël Rapenne and
  • Claire Kammerer

Beilstein J. Org. Chem. 2024, 20, 287–305, doi:10.3762/bjoc.20.30

Graphical Abstract
  • dithienonaphthalene products (e.g., 16) exhibit very different fluorescence properties, S-extrusion from thiophene-annelated thiepines was consequently exploited for peroxide sensing. Very recently, Zhou et al. reported the synthesis of S-doped phenanthrene and triphenylene derivatives via the thermally-induced ring
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Published 15 Feb 2024

Biphenylene-containing polycyclic conjugated compounds

  • Cagatay Dengiz

Beilstein J. Org. Chem. 2023, 19, 1895–1911, doi:10.3762/bjoc.19.141

Graphical Abstract
  • . When the fluorescence properties of compounds 62, 63, and 64 were examined, it was observed that compound 62 exhibited strong fluorescence, making it an excellent fluorophore (λmax,em = 508 nm, Φem = 0.58) . On the other hand, compound 63 showed weaker fluorescence compared to 62 (λmax,em = 666 nm, Φem
  • absorption band, with an onset wavelength at around 570 nm. Although POA 73 does not exhibit any fluorescence characteristics, compound 84 displays a red emission, which can be attributed to the presence of two benzene rings integrated within its structure (λmax,em = 646 nm, Φem = 0.12). The fluorescence
  • properties of the mixture 77/78 were markedly enhanced in comparison to those of linear POAs 73 and 84, owing to the distinctive geometric arrangement inherent in their structures (λmax,em = 506 nm, Φem = 0.65). On-surface synthesis of phenylene-containing oligoacenes The POA syntheses discussed in this
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Published 13 Dec 2023

pH-Responsive fluorescent supramolecular nanoparticles based on tetraphenylethylene-labelled chitosan and a six-fold carboxylated tribenzotriquinacene

  • Nan Yang,
  • Yi-Yan Zhu,
  • Wei-Xiu Lin,
  • Yi-Long Lu and
  • Wen-Rong Xu

Beilstein J. Org. Chem. 2023, 19, 635–645, doi:10.3762/bjoc.19.45

Graphical Abstract
  • powders of CS-TPE exhibit a pale-yellow appearance under normal daylight conditions and emit intense green-blue light when exposed to UV irradiation (365 nm). This phenomenon differs greatly from the fluorescence properties of conventional ACQ fluorophores, which are typically nonfluorescent under UV
  • % (Figure S5, Supporting Information File 1) and TBTQ-C6/CS-TPE-20% (Figure S6, Supporting Information File 1) complexes. Thus, TBTQ-C6/CS-TPE nanoparticles exhibited a high pH response as well as reversible assembly and disassembly capabilities. Fluorescence properties of CS-TPE and TBTQ-C6/CS-TPE in water
  • . The fluorescence properties of CS-TPE and TBTQ-C6/CS-TPE with three different Rf in aqueous medium were investigated by fluorescence spectrophotometry. The fluorescence emission of CS-TPE was significantly enhanced with the increase of its Rf/DL (Figure 7a). This may be caused by the increased
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Published 08 May 2023

Synthesis, optical and electrochemical properties of (D–π)2-type and (D–π)2Ph-type fluorescent dyes

  • Kosuke Takemura,
  • Kazuki Ohira,
  • Taiki Higashino,
  • Keiichi Imato and
  • Yousuke Ooyama

Beilstein J. Org. Chem. 2022, 18, 1047–1054, doi:10.3762/bjoc.18.106

Graphical Abstract
  • and fluorescence maximum wavelengths (λmax,abs and λmax,fl) of OTT-2 appear in a longer wavelength region than those of OTK-2. The fluorescence quantum yield (Φfl) of OTT-2 is 0.41, which is higher than that (Φfl = 0.36) of OTK-2. In the solid state OTT-2 shows relatively intense fluorescence
  • properties (Φfl-solid = 0.24 nm), compared with OTK-2 (Φfl-solid = 0.15 nm). CV results demonstrated that OTT-2 and OTK-2 exhibit a reversible oxidation wave. Based on photoabsorption, fluorescence spectroscopy and CV for the two dyes, it was found that the lowest unoccupied molecular orbital (LUMO) energy
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Published 18 Aug 2022

Morita–Baylis–Hillman reaction of 3-formyl-9H-pyrido[3,4-b]indoles and fluorescence studies of the products

  • Nisha Devi and
  • Virender Singh

Beilstein J. Org. Chem. 2022, 18, 926–934, doi:10.3762/bjoc.18.92

Graphical Abstract
  • and substituents was also studied during investigation of fluorescence properties of these derivatives. Keywords: β-carboline; DABCO; fluorescence; MBH reaction; Michael addition; structure–fluorescence activity relationship; Introduction Among the polycyclic alkaloids based on indole, the tricyclic
  • by evaluation of their fluorescence properties. Results and Discussion The current study began with the synthesis of substituted 3-formyl-9H-β-carbolines (6a–e), which was accomplished by modifying the previously disclosed process as presented in Scheme 1 [46][47][57]. Pictet–Spengler (P-S
  • . Additionally, the scope of the reaction was further extended and the effect of substituents at the N-9 position on the reactivity of 3-formyl-1-aryl-9H-pyrido[3,4-b]indoles was also investigated. Furthermore, fluorescence properties of these β-carboline conjugates were also studied and they were found to
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Published 26 Jul 2022

Post-synthesis from Lewis acid–base interaction: an alternative way to generate light and harvest triplet excitons

  • Hengjia Liu and
  • Guohua Xie

Beilstein J. Org. Chem. 2022, 18, 825–836, doi:10.3762/bjoc.18.83

Graphical Abstract
  • 7 in Figure 5), which consisted of the twisted A–π–D–π–A structure with N-(4-aminophenyl)carbazole (CzPA) as electron donor unit, pyridine as electron acceptor unit, and 9,9-dioctylfluorene (F) as π-conjugated linker [32]. Compound 7 showed remarkable dual-fluorescence properties when mixed with a
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Published 12 Jul 2022

Syntheses of novel pyridine-based low-molecular-weight luminogens possessing aggregation-induced emission enhancement (AIEE) properties

  • Masayori Hagimori,
  • Tatsusada Yoshida,
  • Yasuhisa Nishimura,
  • Yukiko Ogawa and
  • Keitaro Tanaka

Beilstein J. Org. Chem. 2022, 18, 580–587, doi:10.3762/bjoc.18.60

Graphical Abstract
  • thus induced increased fluorescence. The N-methyl-4-((pyridin-2-yl)amino)-substituted maleimides 4a–e comprised an A–D–A system, which exhibited an obvious substitution effect on the fluorescence properties (Figures S18 and S19 in Supporting Information File 1). Although the unsubstituted compound 4a
  • molecules, indicating that fluorescence properties of N-methyl-4-((pyridin-2-yl)amino)-substituted maleimides could be modulated by the electron push–pull effect of substituents. The AIEE properties of products 3a,b, and 4a–e were evaluated in different EtOH/H2O (v/v) solvent mixtures (Table 3 and Figure
  • greatly affected the fluorescence properties of the products, and N-methyl-4-((pyridin-2-yl)amino)-substituted maleimides, containing electron-withdrawing groups formed an A–D–A system and exhibited AIEE properties in aqueous media. In particular, compounds 4a and 4e bearing electron-withdrawing groups
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Published 24 May 2022

Comparative study of thermally activated delayed fluorescent properties of donor–acceptor and donor–acceptor–donor architectures based on phenoxazine and dibenzo[a,j]phenazine

  • Saika Izumi,
  • Prasannamani Govindharaj,
  • Anna Drewniak,
  • Paola Zimmermann Crocomo,
  • Satoshi Minakata,
  • Leonardo Evaristo de Sousa,
  • Piotr de Silva,
  • Przemyslaw Data and
  • Youhei Takeda

Beilstein J. Org. Chem. 2022, 18, 459–468, doi:10.3762/bjoc.18.48

Graphical Abstract
  • and for each relevant electronic state. From these calculations, emission spectra were computed along with fluorescence, phosphorescence, and ISC rates, providing us insight into the mechanism behind the photophysical behavior of the molecules under analysis in this work. Taking fluorescence
  • properties as starting point, the simulations point out considerable similarity between the spectra of the D–A and D–A–D compounds. As shown in Figure S6 (Supporting Information File 1), the calculated fluorescence peaks lie at 510 nm and 505 nm for the D–A and D–A–D compounds, respectively. These results
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Published 25 Apr 2022

Synthesis and investigation on optical and electrochemical properties of 2,4-diaryl-9-chloro-5,6,7,8-tetrahydroacridines

  • Najeh Tka,
  • Mohamed Adnene Hadj Ayed,
  • Mourad Ben Braiek,
  • Mahjoub Jabli and
  • Peter Langer

Beilstein J. Org. Chem. 2021, 17, 2450–2461, doi:10.3762/bjoc.17.162

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  • /bjoc.17.162 Abstract A facile synthesis of 2,4-diaryl-9-chloro-5,6,7,8-tetrahydroacridine derivatives is reported which is based on POCl3-mediated cyclodehydration followed by double Suzuki–Miyaura cross-coupling. The absorption and fluorescence properties of the obtained products were investigated and
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Published 20 Sep 2021

Chemical approaches to discover the full potential of peptide nucleic acids in biomedical applications

  • Nikita Brodyagin,
  • Martins Katkevics,
  • Venubabu Kotikam,
  • Christopher A. Ryan and
  • Eriks Rozners

Beilstein J. Org. Chem. 2021, 17, 1641–1688, doi:10.3762/bjoc.17.116

Graphical Abstract
  • ]. Inspired by these findings, Cheruiyot and Rozners attempted to design fluorescent analogues of 2-aminopyridine; PhEthM (Figure 10) gave the best binding and fluorescence properties, but was strongly quenched upon formation of PNA–dsRNA triplex [147]. In general, quenching of PNA fluorescence upon binding
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Published 19 Jul 2021

2,4-Bis(arylethynyl)-9-chloro-5,6,7,8-tetrahydroacridines: synthesis and photophysical properties

  • Najeh Tka,
  • Mohamed Adnene Hadj Ayed,
  • Mourad Ben Braiek,
  • Mahjoub Jabli,
  • Noureddine Chaaben,
  • Kamel Alimi,
  • Stefan Jopp and
  • Peter Langer

Beilstein J. Org. Chem. 2021, 17, 1629–1640, doi:10.3762/bjoc.17.115

Graphical Abstract
  • of tetrahydroacridines have, to the best of our knowledge, not been studied so far. Recently, our research group reported the synthesis of a large variety of acridine derivatives which showed promising fluorescence properties and high quantum yields [58][59][60]. In continuation of our previous
  • , the methoxy derivative shows promising fluorescence properties. Experimental Materials and measurements All reactions were carried out under an inert argon atmosphere. Anhydrous solvents and chemicals were purchased from Sigma-Aldrich and used without further purification. All reactions were monitored
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Published 16 Jul 2021

Double-headed nucleosides: Synthesis and applications

  • Vineet Verma,
  • Jyotirmoy Maity,
  • Vipin K. Maikhuri,
  • Ritika Sharma,
  • Himal K. Ganguly and
  • Ashok K. Prasad

Beilstein J. Org. Chem. 2021, 17, 1392–1439, doi:10.3762/bjoc.17.98

Graphical Abstract
  • stability, and fluorescence properties. The incorporation of the double-headed nucleosides 151a–d and 154a,b into oligonucleotides failed to form thermostable duplexes with complementary DNA and RNA strands but exhibited a potential resistance towards 3′-exonuclease. The synthesized double-headed
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Published 08 Jun 2021

Tuning the solid-state emission of liquid crystalline nitro-cyanostilbene by halogen bonding

  • Subrata Nath,
  • Alexander Kappelt,
  • Matthias Spengler,
  • Bibhisan Roy,
  • Jens Voskuhl and
  • Michael Giese

Beilstein J. Org. Chem. 2021, 17, 124–131, doi:10.3762/bjoc.17.13

Graphical Abstract
  • . The fluorescence properties noticeably changed from the pristine assemblies directly after removal of the solvent, compared to the materials after one heating/cooling cycle (see Figure 8). In addition, the odd–even effect already described for the liquid crystalline properties also affects the
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Published 14 Jan 2021

Chan–Evans–Lam N1-(het)arylation and N1-alkеnylation of 4-fluoroalkylpyrimidin-2(1H)-ones

  • Viktor M. Tkachuk,
  • Oleh O. Lukianov,
  • Mykhailo V. Vovk,
  • Isabelle Gillaizeau and
  • Volodymyr A. Sukach

Beilstein J. Org. Chem. 2020, 16, 2304–2313, doi:10.3762/bjoc.16.191

Graphical Abstract
  • pyrimidin-2(1H)-ones 5a–e exhibit fluorescence properties with emission of λmax = 490–532 nm in CH2Cl2 solution. In order to analyze the effect exerted on the Chan–Evans–Lam arylation by 4-, 5-, and 6-substituents on the pyrimidine ring and also aiming at the further functionalization of pyrimidin-2(1H)-one
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Published 17 Sep 2020

Styryl-based new organic chromophores bearing free amino and azomethine groups: synthesis, photophysical, NLO, and thermal properties

  • Anka Utama Putra,
  • Deniz Çakmaz,
  • Nurgül Seferoğlu,
  • Alberto Barsella and
  • Zeynel Seferoğlu

Beilstein J. Org. Chem. 2020, 16, 2282–2296, doi:10.3762/bjoc.16.189

Graphical Abstract
  • all dyes 3–7 and 8–12 were recorded in the same solvents of various polarities that were used in the UV–vis studies, and the results are summarized in Table 1 and Table S1 (Supporting Information File 1). All dyes showed fluorescence properties and there was no direct correlation of the increase of
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Published 14 Sep 2020

The B & B approach: Ball-milling conjugation of dextran with phenylboronic acid (PBA)-functionalized BODIPY

  • Patrizia Andreozzi,
  • Lorenza Tamberi,
  • Elisamaria Tasca,
  • Gina Elena Giacomazzo,
  • Marta Martinez,
  • Mirko Severi,
  • Marco Marradi,
  • Stefano Cicchi,
  • Sergio Moya,
  • Giacomo Biagiotti and
  • Barbara Richichi

Beilstein J. Org. Chem. 2020, 16, 2272–2281, doi:10.3762/bjoc.16.188

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  • assemblies had an apolar interior that makes them appealing for encapsulation of organic molecules. Since the assemblies retained the superior biocompatibility of dextran we envisage their use in drug delivery, also profiting from the fluorescence properties of the nanoparticles that could be used to trace
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Published 11 Sep 2020

Et3N/DMSO-supported one-pot synthesis of highly fluorescent β-carboline-linked benzothiophenones via sulfur insertion and estimation of the photophysical properties

  • Dharmender Singh,
  • Vipin Kumar and
  • Virender Singh

Beilstein J. Org. Chem. 2020, 16, 1740–1753, doi:10.3762/bjoc.16.146

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  • chemosensors, ligands, and fluorescent probes. In order to investigate the fluorescence properties, compound 2bA was chosen as the model substrate for optimization of various parameters like time, concentration, and solvent. In order to obtain the maximum emission, various solvents were screened. The
  • presence of two important pharmacophores along with the exocyclic double bond with Michael acceptor properties in the title compounds offers the opportunity to explore their biological potential. Moreover, these β-carboline-linked benzothiophenones displayed excellent fluorescence properties with quantum
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Published 20 Jul 2020

Arylisoquinoline-derived organoboron dyes with a triaryl skeleton show dual fluorescence

  • Vânia F. Pais,
  • Tristan Neumann,
  • Ignacio Vayá,
  • M. Consuelo Jiménez,
  • Abel Ros and
  • Uwe Pischel

Beilstein J. Org. Chem. 2019, 15, 2612–2622, doi:10.3762/bjoc.15.254

Graphical Abstract
  • , boron with sp2 hybridization, such as in triarylboranes, offers the possibility to modulate fluorescence properties by the addition of Lewis bases (e.g., fluoride ions [27][28][29][30][31]) or by exploring the electron-accepting properties of the boron, including charge-transfer and photoinduced
  • , we extended our previously reported arylisoquinoline-derived organoboron dye platform with an additional axially linked aryl residue (see structures 16–19 in Figure 1) in the expectation to modulate the fluorescence properties and fluoride response of these dyes. The additional aryl residues allow
  • does not engage in the formation of an intramolecular Lewis pair, akin to related borylated arylisoquinolines [37][38]. UV–vis absorption and fluorescence properties The absorption and fluorescence properties of the herein investigated dyes 16–19 in air-equilibrated solutions, using three solvents
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Published 04 Nov 2019

A new approach to silicon rhodamines by Suzuki–Miyaura coupling – scope and limitations

  • Thines Kanagasundaram,
  • Antje Timmermann,
  • Carsten S. Kramer and
  • Klaus Kopka

Beilstein J. Org. Chem. 2019, 15, 2569–2576, doi:10.3762/bjoc.15.250

Graphical Abstract
  • intraoperative imaging of cancerous lesions, we were interested in silicon rhodamines due to their fluorescence properties in the biological window (650 nm to 1350 nm). While clinically approved fluorescence dyes like ICG (indocyanine green, Mw = 775 g/mol) have a high molecular weight and could therefore alter
  • dyes Cy5.5 and Alexa Fluor® 680 [23]. Moreover, silicon rhodamines demonstrated in in vivo imaging experiments excellent fluorescence properties and biostabilities [23] as well as exhibited high quantum efficiencies with high tolerance to photobleaching [24]. A silicon rhodamine antibody conjugate
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Published 29 Oct 2019

Ultrafast processes triggered by one- and two-photon excitation of a photochromic and luminescent hydrazone

  • Alessandro Iagatti,
  • Baihao Shao,
  • Alberto Credi,
  • Barbara Ventura,
  • Ivan Aprahamian and
  • Mariangela Di Donato

Beilstein J. Org. Chem. 2019, 15, 2438–2446, doi:10.3762/bjoc.15.236

Graphical Abstract
  • photoswitching mechanism, aimed at characterizing the timescale of the photoinduced structure variation and the solvent dependence of its fluorescence properties, is still lacking. Here we present a spectroscopic characterization of this hydrazone species, using both steady state and time resolved absorption and
  • at room temperature) and can be reverted to the Z-form by irradiation at 340 nm or heat. The molecule also presents peculiar fluorescence properties. Indeed, while the Z-form has an intense emission band peaked at 525 nm in toluene, fluorescence is suppressed for the E-form (Figure 1). The maximum of
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Published 15 Oct 2019

Fluorescent phosphorus dendrimers excited by two photons: synthesis, two-photon absorption properties and biological uses

  • Anne-Marie Caminade,
  • Artem Zibarov,
  • Eduardo Cueto Diaz,
  • Aurélien Hameau,
  • Maxime Klausen,
  • Kathleen Moineau-Chane Ching,
  • Jean-Pierre Majoral,
  • Jean-Baptiste Verlhac,
  • Olivier Mongin and
  • Mireille Blanchard-Desce

Beilstein J. Org. Chem. 2019, 15, 2287–2303, doi:10.3762/bjoc.15.221

Graphical Abstract
  • modifications, on the terminal functions [28][29], at the core [30] or linked to the core [31], and in the branches [32] have been achieved. In this review, we will gather the syntheses, fluorescence properties, and some biological properties of phosphorhydrazone dendrimers bearing in some part of their
  • measurement of the two-photon absorption cross-section, which is a marker of the efficiency of the TPA, displayed a linear increase with the number of fluorophores (Table 1), indicative of an additive behavior. In contrast, the fluorescence properties are only weakly affected. In particular, fluorescence
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Published 24 Sep 2019

Remarkable effect of alkynyl substituents on the fluorescence properties of a BN-phenanthrene

  • Alberto Abengózar,
  • David Sucunza,
  • Patricia García-García and
  • Juan J. Vaquero

Beilstein J. Org. Chem. 2019, 15, 1257–1261, doi:10.3762/bjoc.15.122

Graphical Abstract
  • alkynyl substituents, as their presence in PAHs is known to alter the fluorescence properties thereof markedly [27][28][29]. In this regard, we have recently described a methodology for the synthesis of a chloro-substituted BN-benzo[c]phenanthrene and its subsequent derivatization via palladium-catalyzed
  • of the substituents on the fluorescence properties of the compounds prepared. Results and Discussion Our first aim was to synthesise the Cl-substituted BN-phenanthrene 1b (Scheme 1), following a synthetic sequence analogous to that described previously by us for preparation of the parent BN
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Published 06 Jun 2019

Self-assembly behaviors of perylene- and naphthalene-crown macrocycle conjugates in aqueous medium

  • Xin Shen,
  • Bo Li,
  • Tiezheng Pan,
  • Jianfeng Wu,
  • Yangxin Wang,
  • Jie Shang,
  • Yan Ge,
  • Lin Jin and
  • Zhenhui Qi

Beilstein J. Org. Chem. 2019, 15, 1203–1209, doi:10.3762/bjoc.15.117

Graphical Abstract
  • their UV–vis absorption and fluorescence properties. An unexpected fluorescence quenching phenomenon was observed in the PDI-B21C7 macrocycle conjugate in chloroform. Through TEM characterization, it was illustrated that in aqueous medium, both PDI and NDI derivatives containing crown ether units could
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Published 03 Jun 2019
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