Synthesis and fluorosolvatochromism of 3-arylnaphtho[1,2-b]quinolizinium derivatives

Phil M. Pithan, David Decker, Manlio Sutero Sardo, Giampietro Viola and Heiko Ihmels
Beilstein J. Org. Chem. 2016, 12, 854–862. https://doi.org/10.3762/bjoc.12.84

Supporting Information

The Supporting Information contains the experimental section (synthesis, determination of fluorescence quantum yields); absorption and emission spectra of 6b; 1H NMR spectra of compounds 6ae; plots of emission energies of 6e versus selected solvent parameters; plot of the absorbance of 6c in H2O at λabs = 405 nm versus concentration.

Supporting Information File 1: Experimental and analytical data.
Format: PDF Size: 1004.0 KB Download

Cite the Following Article

Synthesis and fluorosolvatochromism of 3-arylnaphtho[1,2-b]quinolizinium derivatives
Phil M. Pithan, David Decker, Manlio Sutero Sardo, Giampietro Viola and Heiko Ihmels
Beilstein J. Org. Chem. 2016, 12, 854–862. https://doi.org/10.3762/bjoc.12.84

How to Cite

Pithan, P. M.; Decker, D.; Sardo, M. S.; Viola, G.; Ihmels, H. Beilstein J. Org. Chem. 2016, 12, 854–862. doi:10.3762/bjoc.12.84

Download Citation

Citation data can be downloaded as file using the "Download" button or used for copy/paste from the text window below.
Citation data in RIS format can be imported by all major citation management software, including EndNote, ProCite, RefWorks, and Zotero.

Presentation Graphic

Picture with graphical abstract, title and authors for social media postings and presentations.
Format: PNG Size: 367.9 KB Download

Citations to This Article

Up to 20 of the most recent references are displayed here.

Scholarly Works

  • Kawakubo, M.; Inoh, Y.; Inaguma, Y.; Kokubugata, R.; Murata, Y.; Matsumura, M.; Furuno, T.; Yasuike, S. Synthesis and Intracellular Localization of 5,6‐Disubsutituted Pyrido[1′,2′;2,3]imidazo[5,1‐a]isoquinolinium Iodides. ChemistrySelect 2023, 8. doi:10.1002/slct.202303017
  • Belyaev, A.; Su, B.; Cheng, Y.; Liu, Z.; Khan, N. M.; Karttunen, A. J.; Chou, P.; Koshevoy, I. O. Multiple Emission of Phosphonium Fluorophores Harnessed by the Pathways of Photoinduced Counterion Migration. Angewandte Chemie 2022, 134. doi:10.1002/ange.202115690
  • Belyaev, A.; Su, B.-K.; Cheng, Y.-H.; Liu, Z.-Y.; Khan, N. M.; Karttunen, A. J.; Chou, P.-T.; Koshevoy, I. O. Multiple Emission of Phosphonium Fluorophores Harnessed by the Pathways of Photoinduced Counterion Migration. Angewandte Chemie (International ed. in English) 2022, 61, e202115690. doi:10.1002/anie.202115690
  • Wickhorst, P. J.; Druzhinin, S. I.; Ihmels, H.; Müller, M.; Sardo, M. S.; Schönherr, H.; Viola, G. A Dimethylaminophenyl-Substituted Naphtho[1,2-b]quinolizinium as a Multicolor NIR Probe for the Fluorimetric Detection of Intracellular Nucleic Acids and Proteins. ChemPhotoChem 2021, 5, 1079–1088. doi:10.1002/cptc.202100148
  • Lin, T.-C.; Liu, Z.-Y.; Liu, S.-H.; Koshevoy, I. O.; Chou, P.-T. Counterion Migration Driven by Light-Induced Intramolecular Charge Transfer. JACS Au 2021, 1, 282–293. doi:10.1021/jacsau.0c00107
  • Belyaev, A.; Chou, P.-T.; Koshevoy, I. O. Cationic Organophosphorus Chromophores: A Diamond in the Rough among Ionic Dyes. Chemistry (Weinheim an der Bergstrasse, Germany) 2020, 27, 537–552. doi:10.1002/chem.202001853
  • Pithan, P. M.; Steup, S.; Ihmels, H. Cation-induced ring-opening and oxidation reaction of photoreluctant spirooxazine-quinolizinium conjugates. Beilstein journal of organic chemistry 2020, 16, 904–916. doi:10.3762/bjoc.16.82
  • Pithan, P. M.; Ihmels, H. Studies on the photocyclization reaction of 8‐styryl‐substituted coralyne derivatives. Journal of Heterocyclic Chemistry 2020, 57, 1435–1441. doi:10.1002/jhet.3858
  • Schramm, S.; Weiß, D. Fluorescent heterocycles: Recent trends and new developments. Advances in Heterocyclic Chemistry; Elsevier, 2019; Vol. 128, pp 103–179. doi:10.1016/bs.aihch.2018.10.003
  • Bandaru, S. S. M.; Dzubiel, D.; Ihmels, H.; Karbasiyoun, M.; Mahmoud, M. M.; Schulzke, C. Synthesis of 9-arylalkynyl- and 9-aryl-substituted benzo[b]quinolizinium derivatives by Palladium-mediated cross-coupling reactions. Beilstein journal of organic chemistry 2018, 14, 1871–1884. doi:10.3762/bjoc.14.161
  • Lu, F.; Kitamura, N.; Takaya, T.; Iwata, K.; Nakanishi, T.; Kurashige, Y. Experimental and theoretical investigation of fluorescence solvatochromism of dialkoxyphenyl-pyrene molecules. Physical chemistry chemical physics : PCCP 2018, 20, 3258–3264. doi:10.1039/c7cp06811e
  • Pannipara, M.; Al-Sehemi, A. G.; Kalam, A.; Musthafa, T. N. M. Photophysics of Dihydroquinazolinone Derivatives: Experimental and Theoretical Studies. Journal of fluorescence 2017, 27, 1161–1170. doi:10.1007/s10895-017-2051-0
  • Pithan, P. M.; Decker, D.; Sardo, M. S.; Viola, G.; Ihmels, H. Synthesis and Fluorosolvatochromism of 3-Arylnaphtho[1,2-b]quinolizinium Derivatives. ChemInform 2016, 47. doi:10.1002/chin.201630187
Other Beilstein-Institut Open Science Activities