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      A new pH sensitive fluorescent and white light emissive material through controlled intermolecular charge transfer†

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          Abstract

          Fabrication of a unique white light LED from a stimuli-responsive organic molecule is reported. Emission properties are dominated by the pH of the solution through intermolecular charge transfer.

          Abstract

          A new, pH dependent and water-soluble, conjugated oligomer (amino, trimethylammonium oligophenylene vinylene, ATAOPV) was synthesized with a quaternary ammonium salt and an aromatic amine at the two ends of a π-conjugated oligomer, thus creating a strong dipole across the molecule. A unique white light LED is successfully fabricated from a stimuli responsive organic molecule whose emission properties are dominated by the pH value of the solution through controlled intermolecular charge transfer.

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          Most cited references31

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          Visualizing secretion and synaptic transmission with pH-sensitive green fluorescent proteins.

          G Miesenböck, D A De Angelis, J E Rothman (1998)
          In neural systems, information is often carried by ensembles of cells rather than by individual units. Optical indicators provide a powerful means to reveal such distributed activity, particularly when protein-based and encodable in DNA: encodable probes can be introduced into cells, tissues, or transgenic organisms by genetic manipulation, selectively expressed in anatomically or functionally defined groups of cells, and, ideally, recorded in situ, without a requirement for exogenous cofactors. Here we describe sensors for secretion and neurotransmission that fulfil these criteria. We have developed pH-sensitive mutants of green fluorescent protein ('pHluorins') by structure-directed combinatorial mutagenesis, with the aim of exploiting the acidic pH inside secretory vesicles to monitor vesicle exocytosis and recycling. When linked to a vesicle membrane protein, pHluorins were sorted to secretory and synaptic vesicles and reported transmission at individual synaptic boutons, as well as secretion and fusion pore 'flicker' of single secretory granules.
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            Highly sensitive biological and chemical sensors based on reversible fluorescence quenching in a conjugated polymer.

            D Whitten, R Helgeson, Harris Wang … (1999)
            The fluorescence of a polyanionic conjugated polymer can be quenched by extremely low concentrations of cationic electron acceptors in aqueous solutions. We report a greater than million-fold amplification of the sensitivity to fluorescence quenching compared with corresponding "molecular excited states." Using a combination of steady-state and ultrafast spectroscopy, we have established that the dramatic quenching results from weak complex formation [polymer(-)/quencher(+)], followed by ultrafast electron transfer from excitations on the entire polymer chain to the quencher, with a time constant of 650 fs. Because of the weak complex formation, the quenching can be selectively reversed by using a quencher-recognition diad. We have constructed such a diad and demonstrate that the fluorescence is fully recovered on binding between the recognition site and a specific analyte protein. In both solutions and thin films, this reversible fluorescence quenching provides the basis for a new class of highly sensitive biological and chemical sensors.
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              Acridine orange as a probe for measuring pH gradients across membranes: mechanism and limitations.

              M Palmgren (1991)
              Acridine orange is an optical probe commonly used to monitor pH gradients across membranes. In the present study, the changes observed in the visible absorption spectrum of acridine orange during intravesicular acidification of oat root plasma membrane vesicles are shown to be identical with those obtained by increasing the free dye concentration, adding anions, or lowering the temperature, but different from those obtained on addition of biological membranes. It is therefore suggested that the absorbance changes observed during the formation of the pH gradient are simply due to accumulation of free dye inside the vesicles and subsequent dimerization, and not the result of dye-membrane interactions. The proportion of monomeric acridine orange that could undergo dimerization decreased with decreasing temperature. Furthermore, in a membrane-free system different anions induced the formation of dimer-excimer complexes to different degrees. During the formation of the pH gradient permeant anions present in the reaction medium follow the movement of protons into the vesicles, and the intravesicular accumulation of anions thereby amplifies acridine orange quenching, the degree of amplification being dependent on the anion species. Therefore, the use of acridine orange, and probably all metachromatic dyes, as probes for monitoring pH gradients is limited, since these probes neither reflect quantitatively the amount of H+ pumped nor the effect of anions and temperature on transmembrane H+ transport.
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                Author and article information

                Journal
                Journal ID (nlm-ta): Chem Sci
                Journal ID (iso-abbrev): Chem Sci
                Title: Chemical Science
                Publisher: Royal Society of Chemistry
                ISSN (Print): 2041-6520
                ISSN (Electronic): 2041-6539
                Publication date (Print): 1 January 2015
                Publication date (Electronic): 10 September 2014
                Volume: 6
                Issue: 1
                Pages: 789-797
                Affiliations
                [a ] Physical Chemistry and Applied Spectroscopy (C-PCS) , Chemistry Division , Los Alamos National Laboratory , Los Alamos , New Mexico 87545 , USA . Email: hwang@ 123456lanl.gov
                [b ] Theoretical Division , Los Alamos National Laboratory , Los Alamos , New Mexico 87545 , USA . Email: serg@ 123456lanl.gov
                [c ] Department of Chemistry/Display Research Center , Catholic University of Korea , Bucheon 420-743 , Republic of Korea
                [d ] Center for Integrated Nanotechnologies , Materials Physics and Applications Division , Los Alamos National Laboratory , Los Alamos , New Mexico 87545 , USA
                Author notes

                ‡Authors with equal contribution.

                Article
                Publisher ID: c4sc01911c
                DOI: 10.1039/c4sc01911c
                PMC ID: 5592806
                PubMed ID: 28936321
                SO-VID: 2bb34f85-c0d8-42bd-988b-5ac750cae3a0
                Copyright © This journal is © The Royal Society of Chemistry 2014
                License:

                This is an Open Access article distributed under the terms of the Creative Commons Attribution 3.0 Unported License ( http://creativecommons.org/licenses/by/3.0/) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

                History
                Date received : 27 June 2014
                Date accepted : 7 September 2014
                Categories
                Subject: Chemistry

                Notes

                †Electronic supplementary information (ESI) available: Text: experiments, characterization, devices fabrication. Figures: NMR, titration curve, estimation of p K a, single quantum mode fit, absorption/PL spectrum in pH 2/12, different orbitals for molecule A, half-occupied natural orbitals, PL spectra of ATAOPV at different concentrations under different pH, experimental and calculated absorption and emission. See DOI: 10.1039/c4sc01911c


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