Structure and photophysical properties of furoquinoline aza-helicenes: Fluorescence enhancement by protonation

[1]  V. Shirinian,et al.  DABCO‐promoted Selective Photochemical C−N Coupling: Access to Unsymmetrical Azahelicenes , 2023, Advanced Synthesis & Catalysis.

[2]  David E. Herbert When is a Pyridine Not a Pyridine? Benzannulated N-Heterocyclic Ligands in Molecular Materials Chemistry , 2023, Canadian Journal of Chemistry.

[3]  J. Sýkora,et al.  Synthesis of Aza[n]helicenes (n = 4-7) via Photocyclodehydrochlorination of 1-Chloro-N-aryl-2-naphthamides. , 2022, The Journal of organic chemistry.

[4]  L. C. Gonçalves,et al.  Photophysical properties and therapeutic use of natural photosensitizers , 2021 .

[5]  Bing Zheng,et al.  Recent Advances of Furan and Its Derivatives Based Semiconductor Materials for Organic Photovoltaics. , 2021, Small methods.

[6]  A. Zakharov,et al.  Photocyclization of Diarylethenes: The Effect of Electron and Proton Acceptors as Additives. , 2021, The Journal of organic chemistry.

[7]  F. Rominger,et al.  Proving Triptycene Homoconjugation with the Same Chromophore but Different Connectivity to the Core , 2021, Organic Materials.

[8]  K. Radhakrishnan,et al.  Recent Trends in the Synthesis and Mechanistic Implications of Phenanthridines , 2021 .

[9]  Sathiyanarayanan Kulathu Iyer,et al.  Phenanthridine‐Based Donor/Acceptor Fluorescent Dyes: Synthesis, Photophysical Properties and Fluorometric Sensing of Biogenic Primary Amines , 2021 .

[10]  K. Rissanen,et al.  Fluorescence enhancement of quinolines by protonation , 2020, RSC advances.

[11]  G. Kirsch,et al.  Maculine: a furoquinoline alkaloid from the family Rutaceae: sources, syntheses and biological activities , 2020, Arkivoc.

[12]  J. P. S. Ferreira,et al.  Synthesis of 2-aroylfuro[3,2-c]quinolines from quinolone-based chalcones and evaluation of their antioxidant and anticholinesterase activities , 2020 .

[13]  A. Zakharov,et al.  Photochemical rearrangement of diarylethenes: synthesis of functionalized phenanthrenes. , 2020, Organic & biomolecular chemistry.

[14]  Vipin Kumar,et al.  Silver(I)‐Catalyzed Regioselective Synthesis of Dihydrofuro[3,4‐ b ]quinolines from o ‐Alkynylquinoline‐MBH Adducts and Evaluation of their Photophysical Properties , 2020 .

[15]  H. Tian,et al.  Phenanthrene-Fused-Quinoxaline as Key Building Block for Highly Efficient and Stable Sensitizers in Copper Electrolyte Based Dye-Sensitized Solar Cells. , 2020, Angewandte Chemie.

[16]  Patrick McCabe,et al.  Mercury 4.0: from visualization to analysis, design and prediction , 2020, Journal of applied crystallography.

[17]  K. Lyssenko,et al.  Reversible Shifting of a Chemical Equilibrium by Light: The Case of Keto-Enol Tautomerism of a β-Ketoester. , 2019, Organic letters.

[18]  I. Zavarzin,et al.  Photoswitching off the Antiproliferative Activity of Combretastatin A-4 Analogues. , 2019, Organic letters.

[19]  K. Sathiyanarayanan,et al.  Tetrahydrodibenzo[a,i]phenanthridin-5-yl)phenol as fluorescent probe for the detection of Aniline. , 2019, The Journal of organic chemistry.

[20]  Serge A. T. Fobofou,et al.  Furoquinolines and dihydrooxazole alkaloids with cytotoxic activity from the stem bark of Araliopsis soyauxii. , 2019, Fitoterapia.

[21]  Xiaohe Tian,et al.  D-A type phenanthridine derivatives with aggregation-induced enhanced emission and third-order nonlinear optical properties for bioimaging , 2018, Dyes and Pigments.

[22]  F. O'Gara,et al.  Synthesis of Benzofuroquinolines via Phosphine-Free Direct Arylation of 4-Phenoxyquinolines in Air , 2018, European Journal of Organic Chemistry.

[23]  V. Shirinian,et al.  Azole-based diarylethenes as the next step towards advanced photochromic materials , 2018, Journal of Photochemistry and Photobiology C: Photochemistry Reviews.

[24]  Csaba Paizs,et al.  Eco-Friendly Enzymatic Production of 2,5-Bis(hydroxymethyl)furan Fatty Acid Diesters, Potential Biodiesel Additives , 2018, ACS Sustainable Chemistry & Engineering.

[25]  Peng-mian Huang,et al.  Heterocyclic Iodoniums for the Assembly of Oxygen-Bridged Polycyclic Heteroarenes with Water as the Oxygen Source. , 2018, Organic letters.

[26]  Ramakrishna G. Bhat,et al.  A One Pot Transition‐Metal‐Free Synthesis of Styrenyl Ethers from 2‐Aryloxy/Alkoxy Acetophenones , 2018, ChemistrySelect.

[27]  M. Mosslemin,et al.  Synthesis of 3-Aryl-Benzo[b]Furans and 3-Aryl-Naphtho[b]Furans Using N-Propyl-4-Aza-1-Azoniabicyclo[2.2.2]Octane Chloride Immobilised on SiO2 as an Efficient and Reusable Catalyst , 2018 .

[28]  F. Aloui,et al.  Synthesis and characterization of phenanthrene derivatives for optoelectronic applications , 2017 .

[29]  C. Katan,et al.  Luminescence Behavior of Protonated Methoxy-Substituted Diazine Derivatives: Toward White Light Emission , 2016 .

[30]  S. Easwaramoorthi,et al.  Photophysical studies of donor, acceptor substituted tetrahydrodibenzo[a,i]phenanthridines , 2016 .

[31]  O. Fedorova,et al.  Synthesis and spectral properties of fluorescent dyes based on 4-styryl-1,8-naphthalimide , 2016, Russian Chemical Bulletin.

[32]  Yiyuan Peng,et al.  Catalyst-Free Synthesis of 1-Phenylnaphtho[2,1-b]furan Derivatives under Microwave Irradiation , 2016 .

[33]  K. Głowniak,et al.  Furochinoline alkaloids in plants from Rutaceae family – a review , 2016 .

[34]  Xufeng Lin,et al.  Organocatalytic Asymmetric Synthesis of Dihydrobenzoxazinones Bearing Trifluoromethylated Quaternary Stereocenters. , 2016, The Journal of organic chemistry.

[35]  A. Gandini,et al.  Progress of Polymers from Renewable Resources: Furans, Vegetable Oils, and Polysaccharides. , 2016, Chemical reviews.

[36]  Xu-Bo Hu,et al.  Thermally induced formal [3+2] cyclization of ortho-aminoaryl-tethered alkylidenecyclopropanes: facile synthesis of furoquinoline and thienoquinoline derivatives. , 2016, Chemical communications.

[37]  A. Zakharov,et al.  General Photoinduced Sequential Electrocyclization/[1,9]-Sigmatropic Rearrangement/Ring-Opening Reaction of Diarylethenes. , 2015, The Journal of organic chemistry.

[38]  A. Mele,et al.  A Combined Experimental and Theoretical Study on the Stereodynamics of Monoaza[5]helicenes: Solvent-Induced Increase of the Enantiomerization Barrier in 1-Aza-[5]helicene. , 2015, Chemistry.

[39]  Vaibhav N. Khose,et al.  Sterically Congested Chiral 7,8‐Dioxa[6]helicene and Its Dihydro Analogues: Synthesis, Regioselective Functionalization, and Unexpected Domino Prins Reaction , 2015 .

[40]  Mihaela C. Stefan,et al.  Developments of furan and benzodifuran semiconductors for organic photovoltaics , 2015 .

[41]  G. Sheldrick SHELXT – Integrated space-group and crystal-structure determination , 2015, Acta crystallographica. Section A, Foundations and advances.

[42]  G. Sheldrick Crystal structure refinement with SHELXL , 2015, Acta crystallographica. Section C, Structural chemistry.

[43]  I. Piantanida,et al.  Come-back of phenanthridine and phenanthridinium derivatives in the 21st century , 2014, Beilstein journal of organic chemistry.

[44]  R. Singh,et al.  Temperature dependent selective synthesis of linear 2-bromo and 2-alkoxyfuro[2,3-b]quinolines: reaction of 3-(2,2-dibromovinyl-)quinolin-2(1H)-ones with alcoholic KOH , 2014 .

[45]  Yangjie Wu,et al.  Synthesis of ferrocene derivatives with planar chirality via palladium-catalyzed enantioselective C-H bond activation. , 2014, Organic letters.

[46]  T. Kawabata,et al.  Oligonaphthofurans: fan-shaped and three-dimensional π-compounds. , 2014, Journal of the American Chemical Society.

[47]  K. Matsuda,et al.  Facile photochemical synthesis of 5,10-disubstituted [5]helicenes by removing molecular orbital degeneracy. , 2014, Organic letters.

[48]  T. Kawabata,et al.  Synthesis and properties of butterfly-shaped expanded naphthofuran derivatives. , 2014, The Journal of organic chemistry.

[49]  J. Míšek,et al.  On the physicochemical properties of pyridohelicenes. , 2014, Chemistry.

[50]  W. Dehaen,et al.  Oxidative transformation to naphthodithiophene and thia[7]helicenes by intramolecular Scholl reaction of substituted 1,2-bis(2-thienyl)benzene precursors. , 2013, The Journal of organic chemistry.

[51]  Kazunobu Igawa,et al.  Palladium-catalyzed Tandem Cyclodehydrogenation of o-Phenylenediyne-linked Bis(arenol)s to Produce Benzodifuran-containing Condensed Heteroaromatic Ring Systems , 2013 .

[52]  L. Shimon,et al.  Study of a bifuran vs. bithiophene unit for the rational design of π-conjugated systems. What have we learned? , 2013, Chemical communications.

[53]  M. F. D. da Silva,et al.  Furoquinoline alkaloids isolated from Balfourodendron riedelianum as photosynthetic inhibitors in spinach chloroplasts. , 2013, Journal of photochemistry and photobiology. B, Biology.

[54]  H. Doucet,et al.  One-Pot Synthesis of Furo- or Thienoquinolines through Sequential Imination and Intramolecular Palladium-Catalyzed Direct Arylation , 2012 .

[55]  W. Dehaen,et al.  Synthesis and structural elucidation of diversely functionalized 5,10-diaza[5]helicenes. , 2012, The Journal of organic chemistry.

[56]  W. Dehaen,et al.  A fragment-based approach toward substituted trioxa[7]helicenes. , 2012, Organic letters.

[57]  Xin-bing Yu,et al.  Simple and practical synthesis of pyrano- and furano[3,2-c]-quinoline derivatives under non-Lewis acid catalysis , 2012 .

[58]  Chuan-feng Chen,et al.  Helicenes: synthesis and applications. , 2012, Chemical reviews.

[59]  W. Dehaen,et al.  Synthesis of functionalized dioxa-aza[7]helicenes using palladium catalyzed arylations. , 2012, Organic letters.

[60]  K. Müllen,et al.  A High Gain and High Charge Carrier Mobility Indenofluorene‐Phenanthrene Copolymer for Light Amplification and Organic Lasing , 2011, Advanced materials.

[61]  J. Pirani,et al.  Alkaloids from Stems of Esenbeckia leiocarpa Engl. (Rutaceae) as Potential Treatment for Alzheimer Disease , 2010, Molecules.

[62]  Jian-ge Wang,et al.  Syntheses and crystal structures of benzohexathia[7]helicene and naphthalene cored double helicene. , 2010, Organic letters.

[63]  F. Dumitrascu,et al.  Azahelicenes and Other Similar Tri- and Tetracyclic Helical Molecules , 2009 .

[64]  A. Hoerauf,et al.  Antiplasmodial activities of furoquinoline alkaloids from Teclea afzelii , 2009, Phytotherapy research : PTR.

[65]  Richard J. Gildea,et al.  OLEX2: a complete structure solution, refinement and analysis program , 2009 .

[66]  A. Ting,et al.  Fluorescent probes for super-resolution imaging in living cells , 2008, Nature Reviews Molecular Cell Biology.

[67]  N. Lall,et al.  Antimicrobial activity of the methanolic extract and compounds from Teclea afzelii (Rutaceae) , 2008 .

[68]  I. Slaninová,et al.  Quaternary benzo[c]phenanthridine alkaloids—novel cell permeant and red fluorescing DNA probes , 2007, Cytometry. Part A : the journal of the International Society for Analytical Cytology.

[69]  J. Simon,et al.  Solar simulator-induced phototoxicity of the furoquinoline alkaloid dictamnine compared to 8-methoxypsoralen and 5-methoxypsoralen. , 2006, Planta medica.

[70]  N. Monteiro,et al.  A synthetic entry to furo[2,3-b]pyridin-4(1H)-ones and related furoquinolinones via iodocyclization. , 2006, Organic letters.

[71]  C. Tzeng,et al.  Synthesis and anticancer evaluation of certain 4-anilinofuro[2,3-b]quinoline and 4-anilinofuro[3,2-c]quinoline derivatives. , 2005, European journal of medicinal chemistry.

[72]  Marc Litaudon,et al.  Koniamborine, the first pyrano[3,2-b]indole alkaloid and other secondary metabolites from Boronella koniambiensis. , 2005, Journal of natural products.

[73]  R. Tubino,et al.  Synthesis and Characterization of Some Aza[5]helicenes , 2005 .

[74]  N. Luedtke,et al.  On the electronic structure of ethidium. , 2005, Chemistry.

[75]  M. Rashid,et al.  Chemical constituents of Glycosmis arborea: three new carbazole alkaloids and their biological activity. , 2004, Journal of natural products.

[76]  A. Al-Thukair,et al.  Furoquinoline alkaloids from Teclea nobilis. , 2003, Phytochemistry.

[77]  C. Tzeng,et al.  Synthesis and anti-inflammatory evaluation of 9-phenoxyacridine and 4-phenoxyfuro[2,3-b]quinoline derivatives. Part 2. , 2003, Bioorganic & medicinal chemistry.

[78]  R. Haugland,et al.  Rational design and synthesis of a novel class of highly fluorescent rhodamine dyes that have strong absorption at long wavelengths , 2003 .

[79]  D. Curran,et al.  Synthesis of carbocyclic and heterocyclic fused quinolines by cascade radical annulations of unsaturated N-aryl thiocarbamates, thioamides, and thioureas. , 2003, Organic letters.

[80]  Jieping Zhu,et al.  Synthesis of furoquinolines by a multicomponent domino process. , 2002, Angewandte Chemie.

[81]  N. Fokialakis,et al.  Megistoquinones I and II, two quinoline alkaloids with antibacterial activity from the bark of Sarcomelicope megistophylla. , 2002, Chemical & pharmaceutical bulletin.

[82]  J. Zukerman-Schpector,et al.  Biological Activity of Quinoline Alkaloids from Raulinoa echinata and X-ray Structure of Flindersiamine , 2002 .

[83]  K. Möller,et al.  Angular methoxy-substituted furo- and pyranoquinolinones as blockers of the voltage-gated potassium channel Kv1.3. , 2001, Journal of medicinal chemistry.

[84]  Kiyoshi Sato,et al.  Synthesis of novel azonia Helicenes containing terminal thiophene rings , 2000 .

[85]  Rainer Erdmann,et al.  Fast fitting of multi-exponential decay curves , 1997 .

[86]  Lei Liu,et al.  Bromine auxiliaries in photosyntheses of [5]helicenes , 1991 .

[87]  C. W. Mallory,et al.  Photocyclization of stilbenes. VII. Unusual fluorine atom rearrangement in the photocyclization of 1-fluoro[5]helicenes , 1983 .

[88]  I. B. Berlman Empirical study of heavy-atom collisional quenching of the fluorescence state of aromatic compounds in solution , 1973 .

[89]  M. El-Sayed,et al.  The Triplet State and Molecular Electronic Processes in Organic Molecules , 1966 .

[90]  Y. Yokoyama,et al.  Post-modification of the Ethene Bridge in the Rational Design of Photochromic Diarylethenes. , 2019, Chemical record.

[91]  M. Caira,et al.  Pyrroloquinolines, imidazoquinolines, and pyrroloquinazolines with a bridgehead nitrogen , 2019, Advances in Heterocyclic Chemistry.

[92]  S. Tip-Pyang,et al.  New furoquinoline alkaloids from the leaves of Evodia lepta. , 2014, Fitoterapia.

[93]  Lanying Wang,et al.  Synthesis, spectral properties of cell-permeant dimethine cyanine dyes and their application as fluorescent probes in living cell imaging and flow cytometry , 2014 .

[94]  C. Bohne,et al.  Dynamics of guest binding to supramolecular systems: techniques and selected examples , 2007 .

[95]  T. Kubař,et al.  Binding of cationic and neutral phenanthridine intercalators to a DNA oligomer is controlled by dispersion energy: quantum chemical calculations and molecular mechanics simulations. , 2005, Chemistry.

[96]  J. Michael Quinoline, quinazoline and acridone alkaloids. , 2003, Natural product reports.

[97]  J. Michael Quinoline, quinazoline and acridone alkaloids. , 2002, Natural product reports.

[98]  G. Zotti,et al.  Electronic Tuning in C1-Symmetric Chelating Diphosphane Ligands Supported on Stereogenic Aryl-Heteroaryl Templates , 2001 .

[99]  J. Hudson,et al.  Therapeutic potential of plant photosensitizers. , 1991, Pharmacology & therapeutics.

[100]  H. M. Sobell,et al.  Visualization of drug-nucleic acid interactions at atomic resolution. VIII. Structures of two ethidium/dinucleoside monophosphate crystalline complexes containing ethidium: cytidylyl(3'-5') guanosine. , 1984, Journal of biomolecular structure & dynamics.

[101]  A. Bouquet,et al.  Alcaloides d'Araliopsis soyauxii. Isolement d'un nouvel alcaloide, l'Araliopsine , 1976 .