Synthesis and characterization of a dansyl-based fluorescent conjugated polymer

Almeida, Andresa K.A. de; Dias, Jéssica M.M.; Silva, Ana Julia C.; Navarro, Marcelo; Severino, Andrea; Tonholo, Josealdo; Ribeiro, Adriana S.

doi:10.1016/j.synthmet.2013.03.015

Cited by 15 publications

(14 citation statements)

References 47 publications

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“…BFEE is an excellent electrolyte 33,34 and a good solvent 35,36 in which many fused-ring compounds have been electropolymerized successfully. [37][38][39][40] The E ox,m of monomer 1 (0.90 V, Supporting Information Fig. S6) was lower than that of monomer 2 (1.05 V), which was caused by the larger steric hindrance effect of monomer 1 compared with monomer 2.…”

Section: Resultsmentioning

confidence: 99%

High fluorescent ethyl acrylate modified PEDOT‐MeNH₂ with enhanced electrochromic performance

Sun

Zhang

et al. 2016

J. Polym. Sci. Part A: Polym. Chem.

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Two poly(2'-aminomethyl-3,4-ethylenedioxythienylene) (PEDOT-MeNH 2 ) derivatives were successfully synthesized by electrochemical polymerization of precursors, diethyl 3'- (((2,3-dihydrothieno[3,4-b][1,4]dioxin-2-yl) methyl)azanediyl)dipropanoate (monomer 1) and ethyl 3-(((2,3-dihydrothieno[3,4b][1,4]dioxin-2-yl) methyl)amino)propanoate (monomer 2), respectively. Structure-property relationships of monomers and polymers, including electrochemical, optical properties, and morphology, were systematically explored. Significantly, the designed polymers exhibited red and orange emission signatures with high fluorescence quantum yields (U F ) of 0.044 and 0.045 compared with those of monomers; they may be used as building blocks for rational design of fluorescent materials. Moreover, cyclic voltammetry and spectroelectrochemistry studies demonstrated that poly (diethyl 3'-(((2,3-dihydrothieno[3,4-b][1,4]dioxin-2-yl)methyl)azanediyl) dipropanoate) (P1) and poly(ethyl 3-(((2,3-dihydrothieno[3,4b][1,4]dioxin-2-yl)methyl)amino) propanoate) (P2) can be reversibly oxidized and reduced accompanied by obvious color changes from light purple to light blue for P1, and from purple to blue for P2. Furthermore, both P1 and P2 displayed higher optical contrasts (40-70%) in the visible region, favorable coloration efficiency (typically 50-230 cm 2 C 21 ). From these results, the two polymers would be promising candidate materials for display applications.

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Section: Resultsmentioning

confidence: 99%

High fluorescent ethyl acrylate modified PEDOT‐MeNH₂ with enhanced electrochromic performance

Sun

Zhang

et al. 2016

J. Polym. Sci. Part A: Polym. Chem.

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“…The dansyl fluorophore had strong fluorescence emission in the visible region with high quantum yields [18,35]. It consists of two main parts in its molecular structure.…”

Section: Resultsmentioning

confidence: 99%

NITROAROMATIC COMPOUND SENSING APPLICATION OF HEXA-ARMED DANSYL END-CAPPED POLY(epsilon-CAPROLACTONE) STAR POLYMER WITH PHOSPHAZENE CORE

Doğancı¹,

Bayır²,

Doğancı³

et al. 2016

J. Turk. Chem. Soc., Sect. A: Chem.

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Hexa-armed dansyl end-capped poly(ε-caprolactone) star polymer with phosphazene core (N3P3-(PCL-Dansyl)6) was prepared in a two-step synthetic procedure including ring opening polymerization (ROP) of ε-caprolactone (ε-CL) and esterification reactions. The obtained fluorescence-active polymer was employed as a fluorescent probe towards certain nitroaromatic compounds (2,4,6-trinitrotoluene (TNT), 2,4-dinitrotoluene, 2,6-dinitrotoluene, 2-nitrotoluene, 3-nitrotoluene, 2,4,6-trinitrophenol (picric acid), 2,4-dinitrophenol, 4-nitrophenol, and 1,2-dinitrobenzene). Fluorescence intensity of N3P3-(PCL-Dansyl)6 was decreased gradually upon the addition of nitroaromatic compounds and the highest quenching efficiency was found to be 100% with TNT. Besides, N3P3-(PCL-Dansyl)6 gave exceptionally selective response toward nitroaromatic compounds, even in the presence of toxic metal cations such as Pb

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“…It is well known that dansyl derivatives are fluorescent, showing greenish to yellow light emission in the range of 500-550 nm for the fluorophores solubilized in organic solvents, such as, CH 2 Cl 2 and CH 3 CN. 20,22,47,48 PCL is able to interact with the dansyl fluorophores through the formation of hydrogen bonding between the carbonyl group of PCL and the amine or carboxylic acid groups of DnsCad or DnsGly. 49,50 The maximum emission wavelength of the electrospun PCL/fluorophore is hypsochromically shifted compared with the fluorescence maximum of pristine fluorophores, suggesting that such blue-shift is due to the immobilization of the fluorophore within the PCL matrix, as observed by Mocanu et al 51 for the dansyl fluorophore immobilized in alginate and/or cyclodextrin and Zarybnicka et al 52 by applying fluorescent label in polymer nanofibers.…”

Section: Fluorescence Propertiesmentioning

confidence: 99%

“…Our group have synthesized and characterized a series of fluorescent materials based on 1-(dimethylamino)-naphthalene-5-sulfonyl, also known as dansyl, derivatives aiming their application in optoelectronic devices. [20][21][22][23] The dansyl fluorophore exhibits intense absorption bands in the near UV region as well as strong fluorescence in the visible region with high emission quantum yields. 24 Such features, along with the synthetic versatility of the sulfonyl group, aroused considerable interest in preparation of fluorescent electrospun nanofibers for several applications.…”

Section: Introductionmentioning

confidence: 99%

Fluorescent polymer nanofibers based on polycaprolactone and dansyl derivatives for development of latent fingerprints

Júnior

Cantalice

Assis

et al. 2020

J of Applied Polymer Sci

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This work provides a convenient low‐cost strategy for fast fabrication of dansyl‐based fluorescent nanofibers for development of latent fingerprints aiming forensic applications. Polycaprolactone (PCL) and dansyl cadaverine (DnsCad) or dansylglycine (DnsGly) nanofibers are prepared by electrospinning technique and characterized by SEM, FTIR, thermal analysis, and fluorescence spectroscopy. The electrospun PCL/DnsCad and PCL/DnsGly nanofibers are fluorescent with greenish blue and yellowish green emission, respectively. Such nanofibers are useful for enhancement of the visual contrast of latent fingerprints on metallic surfaces when exposed to UV light. These findings are particularly important for development of latent fingerprints on cartridge cases.

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Synthesis and characterization of a dansyl-based fluorescent conjugated polymer

Cited by 15 publications

References 47 publications

High fluorescent ethyl acrylate modified PEDOT‐MeNH₂ with enhanced electrochromic performance

High fluorescent ethyl acrylate modified PEDOT‐MeNH₂ with enhanced electrochromic performance

NITROAROMATIC COMPOUND SENSING APPLICATION OF HEXA-ARMED DANSYL END-CAPPED POLY(epsilon-CAPROLACTONE) STAR POLYMER WITH PHOSPHAZENE CORE

Fluorescent polymer nanofibers based on polycaprolactone and dansyl derivatives for development of latent fingerprints

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Synthesis and characterization of a dansyl-based fluorescent conjugated polymer

Cited by 15 publications

References 47 publications

High fluorescent ethyl acrylate modified PEDOT‐MeNH2 with enhanced electrochromic performance

High fluorescent ethyl acrylate modified PEDOT‐MeNH2 with enhanced electrochromic performance

NITROAROMATIC COMPOUND SENSING APPLICATION OF HEXA-ARMED DANSYL END-CAPPED POLY(epsilon-CAPROLACTONE) STAR POLYMER WITH PHOSPHAZENE CORE

Fluorescent polymer nanofibers based on polycaprolactone and dansyl derivatives for development of latent fingerprints

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High fluorescent ethyl acrylate modified PEDOT‐MeNH₂ with enhanced electrochromic performance

High fluorescent ethyl acrylate modified PEDOT‐MeNH₂ with enhanced electrochromic performance