ArticleThe Journal of organic chemistry2008
Amino(oligo)thiophene-based environmentally sensitive biomembrane chromophores.
Article in The Journal of organic chemistry, 2008. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 19 papers.
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The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.
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Who cites it
19 citing papers in PubMed, 91 citations in OpenAlex.
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- Red-Emitting DithienothiopheneMaterials (Basel, Switzerland) · 2023Article
- Biomimetic lipid-fluorescein probe for cellular bioimaging.Frontiers in chemistry · 2023Article
- Acridine-based dyes as high-performance near-infrared Raman reporter molecules for cell imaging.RSC advances · 2022Article
- Coumarins to Cyanines: Synthesis of Hemicyanines.Organic letters · 2021Article
- Alkynoates as Versatile and Powerful Chemical Tools for the Rapid Assembly of Diverse Heterocycles under Transition-Metal Catalysis: Recent Developments and Challenges.Topics in current chemistry (Cham) · 2021Review
- Methyl Scanning for Mechanochemical Chalcogen-Bonding Cascade Switches.ChemistryOpen · 2020Article
- A Chalcogen-Bonding Cascade Switch for Planarizable Push-Pull Probes.Angewandte Chemie (International ed. in English) · 2019Article
- Rational design of a water-soluble NIR AIEgen, and its application in ultrafast wash-free cellular imaging and photodynamic cancer cell ablation.Chemical science · 2018Article
- Tuning cell surface charge inChemical science · 2016Article
- Article
- Fluorescent flippers for mechanosensitive membrane probes.Journal of the American Chemical Society · 2015Article
- The structural basis for optimal performance of oligothiophene-based fluorescent amyloid ligands: conformational flexibility is essential for spectral assignment of a diversity of protein aggregates.Chemistry (Weinheim an der Bergstrasse, Germany) · 2013Article
- Self-calibrating viscosity probes: design and subcellular localization.Bioorganic & medicinal chemistry · 2012Article
- Action potential propagation in transverse-axial tubular system is impaired in heart failure.Proceedings of the National Academy of Sciences of the United States of America · 2012Article
- Two-photon excited autofluorescence imaging of freshly isolated frog retinas.Biomedical optics express · 2011Article
- Synthesis of acridines by the [4 + 2] annulation of arynes and 2-aminoaryl ketones.The Journal of organic chemistry · 2010Article
- Bichalcophenes: A Concise Synthesis of Formyl Ester- and Cyano Ester-Substituted Bithiophenes, Bifurans, and Furanothiophenes.Journal of heterocyclic chemistry · 2010Article
Corrections and comments
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Authors and funding
4 authors at 1 institution in 1 country.
Funding
Abstract
There is a growing need for cellular imaging with fluorescent probes that emit at longer wavelengths to minimize the effects of absorption, autofluorescence, and scattering from biological tissue. In this paper a series of new environmentally sensitive hemicyanine dyes featuring amino(oligo)thiophene donors have been synthesized via aldol condensation between a 4-methylpyridinium salt and various amino(oligo)thiophene carboxaldehydes, which were, in turn, obtained from amination of bromo(oligo)thiophene carboxaldehyde. Side chains on these fluorophores impart a strong affinity for biological membranes. Compared with benzene analogues, these thiophene fluorophores show significant red shift in the absorption and emission spectra, offering compact red and near-infrared emitting fluorophores. More importantly, both the fluorescence quantum yields and the emission peaks are very sensitive to various environmental factors such as solvent polarity or viscosity, membrane potential, and membrane composition. These chromophores also exhibit strong nonlinear optical properties, including two-photon fluorescence and second harmonic generation, which are themselves environmentally sensitive. The combination of long wavelength fluorescence and nonlinear optical properties make these chromophores very suitable for applications that require sensing or imaging deep inside tissues.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.