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

• 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

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

• 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

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

• 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

Synthesis and fluorescent properties of N(9)-alkylated 2-amino-6-triazolylpurines and 7-deazapurines

• Andrejs Šišuļins,
• Jonas Bucevičius,
• Yu-Ting Tseng,
• Irina Novosjolova,
• Kaspars Traskovskis,
• Ērika Bizdēna,
• Huan-Tsung Chang,
• Sigitas Tumkevičius and
• Māris Turks

Beilstein J. Org. Chem. 2019, 15, 474–489, doi:10.3762/bjoc.15.41

• transformed into the title compounds by CuAAC reaction. The designed compounds belong to the push–pull systems and possess promising fluorescence properties with quantum yields in the range from 28% to 60% in acetonitrile solution. Due to electron-withdrawing properties of purine and 7-deazapurine

Ring-closing-metathesis-based synthesis of annellated coumarins from 8-allylcoumarins

• Christiane Schultze and
• Bernd Schmidt

Beilstein J. Org. Chem. 2018, 14, 2991–2998, doi:10.3762/bjoc.14.278

• course of this study were previously described in the literature: compound 15a was used to investigate the regioselectivity of [2 + 2]-photocycloadditions [71], compound 15d was included in a comparative investigation into the fluorescence properties of 4-methylcoumarins [72], compounds 15b and 15c were

Rational design of boron-dipyrromethene (BODIPY) reporter dyes for cucurbit[7]uril

• Mohammad A. Alnajjar,
• Jürgen Bartelmeß,
• Robert Hein,
• Pichandi Ashokkumar,
• Mohamed Nilam,
• Werner M. Nau,
• Knut Rurack and
• Andreas Hennig

Beilstein J. Org. Chem. 2018, 14, 1961–1971, doi:10.3762/bjoc.14.171

• fluorescent dyes directly enables (bio)sensing applications through the indicator displacement principle [16][17]. Therein, the fluorescence properties of a dye are altered when encapsulated by the host, and when a competitive binder displaces the dye from the cavity, the properties of the non-encapsulated

• applicable to pH-sensitive fluoresceins, cyanines or rhodamines, in which protonation and deprotonation of suitably positioned amino groups can also modulate their fluorescence properties. It can also be used to design dyes which reduce their fluorescence upon binding, e.g., when electron-poor groups are

Fluorogenic PNA probes

• Tirayut Vilaivan

Beilstein J. Org. Chem. 2018, 14, 253–281, doi:10.3762/bjoc.14.17

• applications, it means that tC–PNA alone is not useful as a fluorogenic probe. The related tri- or bicyclic thymine analogues tT and bT (without the additional aromatic ring) pair specifically with dA when incorporated into aegPNA, but their fluorescence properties have not been reported [184]. PNA carrying

• phenoxazine analogues of tC (tCO) with a positively-charged pendant (so-called "G-clamp") were prepared in order to improve the affinity of PNA–DNA duplex by additional hydrogen bonding [185][186][187]. No fluorescence properties of these tCO-based G-clamps PNA have been reported, but it is quite likely that

Fluorescent nucleobase analogues for base–base FRET in nucleic acids: synthesis, photophysics and applications

• Mattias Bood,
• Sangamesh Sarangamath,
• Moa S. Wranne,
• Morten Grøtli and
• L. Marcus Wilhelmsson

Beilstein J. Org. Chem. 2018, 14, 114–129, doi:10.3762/bjoc.14.7

• distances that can be monitored range between 15–90 Å which well match the dimensions of biomolecules. The efficiency of an energy-transfer process (E, between 0 and 100%) can be established using either steady-state or time-resolved fluorescence spectroscopy by comparing fluorescence properties with and

• (Scheme 9 and Scheme 10) [55][56]. As monomers, these compounds show significantly improved fluorescence properties. Importantly, one of the derivatives, qAN1, showed a high quantum yield in water (18%) that was not excessively influenced by varying the solvent, indicating that qAN1 is not highly

Pyrene–nucleobase conjugates: synthesis, oligonucleotide binding and confocal bioimaging studies

• Artur Jabłoński,
• Yannic Fritz,
• Hans-Achim Wagenknecht,
• Rafał Czerwieniec,
• Tytus Bernaś,
• Damian Trzybiński,
• Krzysztof Woźniak and
• Konrad Kowalski

Beilstein J. Org. Chem. 2017, 13, 2521–2534, doi:10.3762/bjoc.13.249

• characterized. X-ray single-crystal structure analysis performed for the pyrene–C(O)CH2CH2–thymine (2) conjugate reveals dimers of molecules 2 stabilized by hydrogen bonds between the thymine moieties. The photochemical characterization showed structure-dependent fluorescence properties of the investigated

• structure of 2 and full list of bond lengths and angles are given in Supporting Information File 1 (Table S3, Table S4, and Figure S6). Photophysical characterization and DFT calculations UV–vis absorption and fluorescence properties of pyrene–nucleobase conjugates 2–5 were characterized in dichloromethane

Synthesis and photophysical properties of novel benzophospholo[3,2-b]indole derivatives

• Mio Matsumura,
• Mizuki Yamada,
• Atsuya Muranaka,
• Misae Kanai,
• Naoki Kakusawa,
• Daisuke Hashizume,
• Masanobu Uchiyama and
• Shuji Yasuike

Beilstein J. Org. Chem. 2017, 13, 2304–2309, doi:10.3762/bjoc.13.226

• fluorescence properties with respect to the intensity. Complex 9 exhibited a high quantum yield (Ф = 75%), while complex 8 exhibited a weak emission (Ф = 11%). In these fluorescence spectra of compounds 4–7, a vibronic band was detected as a shoulder peak around 530 nm. In the case of phosphonium cation 7, the

Curcuminoid–BF₂ complexes: Synthesis, fluorescence and optimization of BF₂ group cleavage

• Henning Weiss,
• Jeannine Reichel,
• Helmar Görls,
• Kilian Rolf Anton Schneider,
• Mathias Micheel,
• Michael Pröhl,
• Michael Gottschaldt,
• Benjamin Dietzek and
• Wolfgang Weigand

Beilstein J. Org. Chem. 2017, 13, 2264–2272, doi:10.3762/bjoc.13.223

• phenyl ring, the presence of an additional electron-donating methoxy group has almost no impact on the fluorescence properties. Conclusion We have synthesized a series of novel curcuminoid–BF2 complexes by an improved synthetic route. All complexes were received in high yields and purities and

Fluorescent carbon dots from mono- and polysaccharides: synthesis, properties and applications

• Stephen Hill and
• M. Carmen Galan

Beilstein J. Org. Chem. 2017, 13, 675–693, doi:10.3762/bjoc.13.67

• their in vivo applications are restricted [12]. Therefore, the development of fluorescent nanoparticles that are able to replicate QD fluorescence properties without exhibiting long term toxicity profiles, has become very relevant. The term carbon dots (CDs) has been coined to describe a new class of

• tuneable synthesis of FCDs by selecting a different inorganic ion and carbohydrate combinations using microwave irradiation as the heating source, demonstrating that both the starting material and dehydrating agent of choice can allow tuning/manipulation of the fluorescence properties of the system [31

• -speed liquid jets in solution. All of these effects facilitate the degradation of glucose and the incorporation of ammonia into the CD structure. The introduction of N-doping allows the injection of electrons into the CD structure, which allows for new PL and fluorescence properties to be established

Novel β-cyclodextrin–eosin conjugates

• Gábor Benkovics,
• Damien Afonso,
• András Darcsi,
• Szabolcs Béni,
• Sabrina Conoci,
• Éva Fenyvesi,
• Lajos Szente,
• Milo Malanga and
• Salvatore Sortino

Beilstein J. Org. Chem. 2017, 13, 543–551, doi:10.3762/bjoc.13.52

• -cyclodextrin–EoY conjugate retains both the fluorescence properties and the capability to photogenerate singlet oxygen of the unbound chromophore. In contrast, the corresponding β-cyclodextrin–EoB conjugate did not show either relevant emission or photosensitizing activity probably due to aggregation in

A postsynthetically 2’-“clickable” uridine with arabino configuration and its application for fluorescent labeling and imaging of DNA

• Heidi-Kristin Walter,
• Bettina Olshausen,
• Ute Schepers and
• Hans-Achim Wagenknecht

Beilstein J. Org. Chem. 2017, 13, 127–137, doi:10.3762/bjoc.13.16

• yield. Especially mixed combinations, that means donor dyes with arabino-configured anchor with acceptor dyes with ribo-configured anchor, and vice versa, showed significantly improved fluorescence properties. Those were successfully applied for fluorescent imaging of DNA after transport into living

Benzothiadiazole oligoene fatty acids: fluorescent dyes with large Stokes shifts

• Lukas J. Patalag and
• Daniel B. Werz

Beilstein J. Org. Chem. 2016, 12, 2739–2747, doi:10.3762/bjoc.12.270

• ., differences in membrane thickness and stiffness, different diffusion coefficients etc.) [5][6]. Tools to investigate lipid membranes are multifaceted; however, all optical methods are hampered by the missing absorption and fluorescence properties of natural occurring lipid components. Therefore, indirect

Synthesis and properties of fluorescent 4′-azulenyl-functionalized 2,2′:6′,2″-terpyridines

• Adrian E. Ion,
• Liliana Cristian,
• Mariana Voicescu,
• Masroor Bangesh,
• Augustin M. Madalan,
• Daniela Bala,
• Constantin Mihailciuc and
• Simona Nica

Beilstein J. Org. Chem. 2016, 12, 1812–1825, doi:10.3762/bjoc.12.171

• by comparison with analogues ruthenium complexes with unsubstituted or 4′-phenyl-substituted terpyridine. In this contribution we report on the green synthesis and physicochemical investigations of the 4′-azulenyl-substituted terpyridines with particular interest on the fluorescence properties. The

• their polarization vectors. TDDFT calculations showed that the fluorescence properties are determined by azulene-centered valence-state excitation and azulene→terpyridine charge-transfer transitions. Both compounds exhibit electrochemical behavior with one-electron oxidation/reduction steps, which can

Application of Cu(I)-catalyzed azide–alkyne cycloaddition for the design and synthesis of sequence specific probes targeting double-stranded DNA

• Svetlana V. Vasilyeva,
• Vyacheslav V. Filichev and
• Alexandre S. Boutorine

Beilstein J. Org. Chem. 2016, 12, 1348–1360, doi:10.3762/bjoc.12.128

• synthesis protocol and characteristics are described in Supporting Information File 1, Table S1. Fluorescence properties of the probes were studied in the experiments on titration of the probes by the target DNA duplex (presented on Figure 5A). As it is seen in Figure 8, the fluorescence of the probes

Synthesis, fluorescence properties and the promising cytotoxicity of pyrene–derived aminophosphonates

• Jarosław Lewkowski,
• Maria Rodriguez Moya,
• Anna Wrona-Piotrowicz,
• Janusz Zakrzewski,
• Renata Kontek and
• Gabriela Gajek

Beilstein J. Org. Chem. 2016, 12, 1229–1235, doi:10.3762/bjoc.12.117

• , University of Łódź, Banacha 12/16, 90-237 Łódź, Poland 10.3762/bjoc.12.117 Abstract A large series of variously substituted amino(pyren-1-yl)methylphosphonic acid derivatives was synthesized using a modified aza-Pudovik reaction in 20–97% yields. The fluorescence properties of the obtained compounds were

• normal lymphocytes (IC50 = 230.8 µM). Keywords: aminophosphonic derivatives; cytotoxicity; fluorescence properties; MTT test; pyrene-1-carboxaldehyde; Introduction The biological activity of aminophosphonic systems is very well known and described, in aspect of their crop protective [1], antibacterial

• phosphonates. Recently, an Indian group [9] reported the synthesis of a number of N-aryl substituted, diethyl amino(pyrene-1-yl)methyl phosphonates and some preliminary studies on their fluorescence properties. Such a poor knowledge about these compounds is astonishing in the light of the fact that the

Interactions of cyclodextrins and their derivatives with toxic organophosphorus compounds

• Sophie Letort,
• Sébastien Balieu,
• William Erb,
• Géraldine Gouhier and
• François Estour

Beilstein J. Org. Chem. 2016, 12, 204–228, doi:10.3762/bjoc.12.23

• -CD aqueous solutions upon the fluorescence properties of pirimiphos-methyl (6, Figure 3) were also investigated [46]. As the inclusion phenomena occur, it is reported that the fluorescence properties of the guest are improved compared to its free form in aqueous solution. For both β- or HP-β-CD, the

• estimate the binding constants of 171 M−1 and 736 M−1 for β- and HP-β-CD, respectively. In presence of HP-β-CD, the fluorescence properties of azinphos-methyl (AZM, 7, Figure 3) were improved by a factor of three but even if it induces a higher fluorescence enhancement than β-CD, this remains too weak to

Dicarboxylic esters: Useful tools for the biocatalyzed synthesis of hybrid compounds and polymers

• Ivan Bassanini,
• Karl Hult and
• Sergio Riva

Beilstein J. Org. Chem. 2015, 11, 1583–1595, doi:10.3762/bjoc.11.174

• synthesis with carbinol (hydroxy) terminated polydimethylsiloxane catalyzed by CAL-B [67]. The curcumin moiety retained its fluorescence properties without quenching in thin films prepared from the polymer. Films exposed to low concentrations of vapors of the explosives DNT and TNT absorbed the explosives

Synthesis and spectroscopic properties of β-triazoloporphyrin–xanthone dyads

• Dileep Kumar Singh and
• Mahendra Nath

Beilstein J. Org. Chem. 2015, 11, 1434–1440, doi:10.3762/bjoc.11.155

• ] including anti-oxidative [35], antihypertensive [36], anti-inflammatory [37] and antiplatelet agents [38]. They have also been used as fluorophores and exhibited good fluorescence properties when attached to a triazole ring [39][40]. Owing to the biological significance of porphyrins, 1,2,3-triazoles and

Indolizines and pyrrolo[1,2-c]pyrimidines decorated with a pyrimidine and a pyridine unit respectively

• Marcel Mirel Popa,
• Emilian Georgescu,
• Mino R. Caira,
• Florentina Georgescu,
• Constantin Draghici,
• Raluca Stan,
• Calin Deleanu and
• Florea Dumitrascu

Beilstein J. Org. Chem. 2015, 11, 1079–1088, doi:10.3762/bjoc.11.121

• structurally characterized by NMR spectroscopy. The biological and fluorescence properties of the new synthesized compounds will be intensely investigated further. Reported methods were employed in obtaining the 4-pyridylpyrimidine isomers used as starting materials. X-ray analyses of the 4-pyridylpyrimidines

A small azide-modified thiazole-based reporter molecule for fluorescence and mass spectrometric detection

• Stefanie Wolfram,
• Hendryk Würfel,
• Stefanie H. Habenicht,
• Christine Lembke,
• Phillipp Richter,
• Eckhard Birckner,
• Rainer Beckert and
• Georg Pohnert

Beilstein J. Org. Chem. 2014, 10, 2470–2479, doi:10.3762/bjoc.10.258

• )thiazol-4-ol (4). This derivative of the 4-hydroxythiazole family was already synthesized by Beckert et al. in a study focusing on the fluorescence properties of 4-hydroxythiazoles [29]. It exhibits an intense bathochromic shift of the UV–vis absorption when deprotonated at the 4-hydroxy position. The

Synthesis and optical properties of pyrrolidinyl peptide nucleic acid carrying a clicked Nile red label

• Nattawut Yotapan,
• Chayan Charoenpakdee,
• Pawinee Wathanathavorn,
• Boonsong Ditmangklo,
• Hans-Achim Wagenknecht and
• Tirayut Vilaivan

Beilstein J. Org. Chem. 2014, 10, 2166–2174, doi:10.3762/bjoc.10.224

• insertion in close proximity to the Nile red label. The results indicate that the Nile red label is located in a more hydrophobic environment in acpcPNA–DNA duplexes than in the single-stranded acpcPNA. The different fluorescence properties of the acpcPNA hybrids of complementary DNA and DNA carrying a base

Synthesis of 2-substituted tryptophans via a C3- to C2-alkyl migration

• Michele Mari,
• Simone Lucarini,
• Francesca Bartoccini,
• Giovanni Piersanti and
• Gilberto Spadoni

Beilstein J. Org. Chem. 2014, 10, 1991–1998, doi:10.3762/bjoc.10.207

• ]. Tryptophan and tryptophan analogs also have applications in chemical biology thanks to the highly environment-sensitive fluorescence properties of the indole ring [8][9][10][11][12][13][14][15][16][17] and when incorporated into peptides, they lead to compounds with increased resistance to enzymatic