Photophysical properties of push–pull 8-aryl-deoxyguanosine probes within duplex and G-quadruplex structures

2016 ◽  
Vol 4 (14) ◽  
pp. 2915-2924 ◽  
Author(s):  
Darian J. M. Blanchard ◽  
Kaila L. Fadock ◽  
Michael Sproviero ◽  
Prashant S. Deore ◽  
Thomas Z. Cservenyi ◽  
...  
Keyword(s):  
Photophysical Properties ◽  
Sensing Applications ◽  
G Quadruplex ◽  
Viscosity Sensing

Acceptor aryl groups at the 8-position of 2′-deoxyguanosine (dG) generate visibly emissive 8aryldG probes, which provide viscosity-sensing applications within oligonucleotides.

Photophysical properties and pH sensing applications of luminescent salicylaldehyde derivatives

2015 ◽  
Vol 42 (5) ◽  
pp. 5027-5048 ◽  
Author(s):  
Jiaoyan Liu ◽  
Jinghui Cheng ◽  
Xiaofeng Ma ◽  
Xiangge Zhou ◽  
Haifeng Xiang
Keyword(s):  
Photophysical Properties ◽  
Ph Sensing ◽  
Sensing Applications ◽  
Salicylaldehyde Derivatives

scholarly journals Toward Prediction of Nonradiative Decay Pathways in Organic Compounds II: Two Internal Conversion Channels in BODIPYs

2019 ◽  
Author(s):  
Zhou Lin ◽  
Alexander Kohn ◽  
Troy Van Voorhis
Keyword(s):  
Quantum Yield ◽  
Rational Design ◽  
Internal Conversion ◽  
Photophysical Properties ◽  
Data Driven ◽  
Laser Dyes ◽  
Intermediate Structure ◽  
Sensing Applications ◽  
Aided Design ◽  
Semi Empirical

<div>Boron-dipyrromethene (BODIPY) molecules are widely used as laser dyes and have therefore become a popular research topic within recent decades. Numerous studies have been reported for the rational design of BODIPY derivatives based on their spectroscopic and photophysical properties, including absorption and fluorescence wavelengths (<i>λ</i><sub>abs</sub> and <i>λ</i><sub>fl</sub>), oscillator strength (<i>f</i>), nonradiative pathways, and quantum yield (<i>ϕ</i>). In the present work, we illustrate a theoretical, semi-empirical model that accurately predicts <i>ϕ</i> for various BODIPY compounds based on inexpensive electronic structure calculations, following the data-driven algorithm proposed and tested on the naphthalene family by us [Kohn, Lin, and Van Voorhis, <i>J. Phys. Chem. C.</i> <b>2019</b>, <i>123</i>, 15394]. The model allows us to identify the dominant nonradiative channel of any BODIPY molecule using its structure exclusively and to establish a correlation between the activation energy (<i>E</i><sub>a</sub>) and the fluorescence quantum yield (<i>ϕ</i><sub>fl</sub>). Based on our calculations, either the S<sub>1</sub> → S<sub>0</sub> or <i>L<sub>a</sub></i> → <i>L<sub>b</sub></i> internal conversion (IC) mechanism dominates in the majority of BODIPY derivatives, depending on the structural and electronic properties of the substituents. In both cases, the nonradiative rate (<i>k</i><sub>nr</sub>) exhibits a straightforward Arrhenius-like relation with the associated <i>E</i><sub>a</sub>. More interestingly, the S<sub>1</sub> → S<sub>0</sub> mechanism proceeds via a highly distorted intermediate structure in which the core BODIPY plane and the substituent at the 1-position are forced to bend, while the internal rotation of the very same substituent induces the <i>La </i>→<i> Lb</i> transition. Our model reproduces <i>k</i><sub>fl</sub>, <i>k</i><sub>nr</sub>, and <i>ϕ</i><sub>fl</sub> to mean absolute errors (MAE) of 0.16 decades, 0.87 decades, and 0.26, when all outliers are considered. These results allow us to validate the predictive power of the proposed data-driven algorithm in <i>ϕ</i><sub>fl</sub>. They also indicate that the model has a great potential to facilitate and accelerate the machine learning aided design of BODIPY dyes for imaging and sensing applications, given sufficient experimental data and appropriate molecular descriptors.</div>

scholarly journals Toward Prediction of Nonradiative Decay Pathways in Organic Compounds II: Two Internal Conversion Channels in BODIPYs

2019 ◽  
Author(s):  
Zhou Lin ◽  
Alexander Kohn ◽  
Troy Van Voorhis
Keyword(s):  
Quantum Yield ◽  
Rational Design ◽  
Internal Conversion ◽  
Photophysical Properties ◽  
Data Driven ◽  
Laser Dyes ◽  
Intermediate Structure ◽  
Sensing Applications ◽  
Aided Design ◽  
Semi Empirical

<div>Boron-dipyrromethene (BODIPY) molecules are widely used as laser dyes and have therefore become a popular research topic within recent decades. Numerous studies have been reported for the rational design of BODIPY derivatives based on their spectroscopic and photophysical properties, including absorption and fluorescence wavelengths (<i>λ</i><sub>abs</sub> and <i>λ</i><sub>fl</sub>), oscillator strength (<i>f</i>), nonradiative pathways, and quantum yield (<i>ϕ</i>). In the present work, we illustrate a theoretical, semi-empirical model that accurately predicts <i>ϕ</i> for various BODIPY compounds based on inexpensive electronic structure calculations, following the data-driven algorithm proposed and tested on the naphthalene family by us [Kohn, Lin, and Van Voorhis, <i>J. Phys. Chem. C.</i> <b>2019</b>, <i>123</i>, 15394]. The model allows us to identify the dominant nonradiative channel of any BODIPY molecule using its structure exclusively and to establish a correlation between the activation energy (<i>E</i><sub>a</sub>) and the fluorescence quantum yield (<i>ϕ</i><sub>fl</sub>). Based on our calculations, either the S<sub>1</sub> → S<sub>0</sub> or <i>L<sub>a</sub></i> → <i>L<sub>b</sub></i> internal conversion (IC) mechanism dominates in the majority of BODIPY derivatives, depending on the structural and electronic properties of the substituents. In both cases, the nonradiative rate (<i>k</i><sub>nr</sub>) exhibits a straightforward Arrhenius-like relation with the associated <i>E</i><sub>a</sub>. More interestingly, the S<sub>1</sub> → S<sub>0</sub> mechanism proceeds via a highly distorted intermediate structure in which the core BODIPY plane and the substituent at the 1-position are forced to bend, while the internal rotation of the very same substituent induces the <i>La </i>→<i> Lb</i> transition. Our model reproduces <i>k</i><sub>fl</sub>, <i>k</i><sub>nr</sub>, and <i>ϕ</i><sub>fl</sub> to mean absolute errors (MAE) of 0.16 decades, 0.87 decades, and 0.26, when all outliers are considered. These results allow us to validate the predictive power of the proposed data-driven algorithm in <i>ϕ</i><sub>fl</sub>. They also indicate that the model has a great potential to facilitate and accelerate the machine learning aided design of BODIPY dyes for imaging and sensing applications, given sufficient experimental data and appropriate molecular descriptors.</div>

scholarly journals Recent Progress in Metal–Organic Framework (MOF) Based Luminescent Chemodosimeters

Nanomaterials ◽  
2019 ◽  
Vol 9 (7) ◽  
pp. 974 ◽  
Author(s):  
Hao ◽  
Chen ◽  
Zhou ◽  
Zhang ◽  
Xu
Keyword(s):  
Photophysical Properties ◽  
Metal Organic Framework ◽  
Organic Ligands ◽  
Future Perspectives ◽  
Fluoride Ions ◽  
Luminescent Sensors ◽  
Sensing Applications ◽  
Redox Active ◽  
Metal Organic ◽  
Luminescent Sensing

Metal–organic frameworks (MOFs), as a class of crystalline hybrid architectures, consist of metal ions and organic ligands and have displayed great potential in luminescent sensing applications due to their tunable structures and unique photophysical properties. Until now, many studies have been reported on the development of MOF-based luminescent sensors, which can be classified into two major categories: MOF chemosensors based on reversible host–guest interactions and MOF chemodosimeters based on the irreversible reactions between targets with a probe. In this review, we summarize the recently developed luminescent MOF-based chemodosimeters for various analytes, including H2S, HClO, biothiols, fluoride ions, redox-active biomolecules, Hg2+, and CN−. In addition, some remaining challenges and future perspectives in this area are also discussed.

scholarly journals Terpyridine-Functionalized Calixarenes: Synthesis, Characterization and Anion Sensing Applications

Molecules ◽  
2020 ◽  
Vol 26 (1) ◽  
pp. 87
Author(s):  
Nicola Y. Edwards ◽  
David M. Schnable ◽  
Ioana R. Gearba-Dolocan ◽  
Jenna L. Strubhar
Keyword(s):  
Photophysical Properties ◽  
Binding Constants ◽  
Molar Absorptivity ◽  
Quantum Yields ◽  
Anion Sensing ◽  
Fluorescence Studies ◽  
Sensing Applications ◽  
Amide Coupling ◽  
Vis Spectroscopy ◽  
Arene Ligand

Lanthanide complexes have been developed and are reported herein. These complexes were derived from a terpyridine-functionalized calix[4]arene ligand, chelated with Tb3+ and Eu3+. Synthesis of these complexes was achieved in two steps from a calix[4]arene derivative: (1) amide coupling of a calix[4]arene bearing carboxylic acid functionalities and (2) metallation with a lanthanide triflate salt. The ligand and its complexes were characterized by NMR (1H and 13C), fluorescence and UV-vis spectroscopy as well as MS. The photophysical properties of these complexes were studied; high molar absorptivity values, modest quantum yields and luminescence lifetimes on the ms timescale were obtained. Anion binding results in a change in the photophysical properties of the complexes. The anion sensing ability of the Tb(III) complex was evaluated via visual detection, UV-vis and fluorescence studies. The sensor was found to be responsive towards a variety of anions, and large binding constants were obtained for the coordination of anions to the sensor.

Five concomitant polymorphs of a green fluorescent protein chromophore (GFPc) analogue: understanding variations in photoluminescence with π-stacking interactions

2020 ◽  
Vol 76 (5) ◽  
pp. 850-864
Author(s):  
Bhupendra P. Mali ◽  
Soumya Ranjan Dash ◽  
Shrikant B. Nikam ◽  
Anisha Puthuvakkal ◽  
Kumar Vanka ◽  
...  
Keyword(s):  
Green Fluorescent Protein ◽  
Smart Materials ◽  
Fluorescent Protein ◽  
Photophysical Properties ◽  
Carbonyl Oxygen ◽  
Stacking Interactions ◽  
Subtle Difference ◽  
Sensing Applications ◽  
Π Stacking ◽  
Green Fluorescent

The synthetically modified green fluorescent protein chromophore analogue 3,4,5-trimethoxybenzylidene imidazolinone (1) yielded five polymorphs (I, II, III, IV, V) concomitantly irrespective of the solvent used for crystallization. The pentamorphic modification of 1 is solely due to the interplay of iso-energetic weak intermolecular interactions in molecular associations as well as the conformational flexibility offered by a C—C single bond, which connects the electron-deficient moiety imidazolinone with the electron-rich trimethoxybenzylidene group. A common structural feature observed in all the polymorphs is the formation of a `zero-dimensional' centrosymmetric dimeric unit through a short and linear C—H...O hydrogen bond engaging phenyl C—H and imidazolinone carbonyl oxygen. However, the networking of these dimeric units showed a subtle difference in all the polymorphs. The 2D isostructurality was observed between polymorphs I, II and III, while the other two polymorphs IV and V revealed only `zero-dimensional' isostructurality. The different fluorescence emissions of Form I (blue) and Forms II to V (yellow) were attributed to the differences in π-stacking interactions. It shows that one can modulate the photophysical properties of these smart materials by slightly altering their crystal structure. Such an approach will aid in developing new multi-colour organic fluorescent materials of varying crystal structures for live-cell imaging and fluorescent sensing applications.

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