Show/Hide Menu
Hide/Show Apps
Logout
Türkçe
Türkçe
Search
Search
Login
Login
OpenMETU
OpenMETU
About
About
Open Science Policy
Open Science Policy
Open Access Guideline
Open Access Guideline
Postgraduate Thesis Guideline
Postgraduate Thesis Guideline
Communities & Collections
Communities & Collections
Help
Help
Frequently Asked Questions
Frequently Asked Questions
Guides
Guides
Thesis submission
Thesis submission
MS without thesis term project submission
MS without thesis term project submission
Publication submission with DOI
Publication submission with DOI
Publication submission
Publication submission
Supporting Information
Supporting Information
General Information
General Information
Copyright, Embargo and License
Copyright, Embargo and License
Contact us
Contact us
Polycyclic aromatic hydrocarbon-substituted push-pull chromophores: an investigation of optoelectronic and nonlinear optical properties using experimental and theoretical approaches
Date
2021-01-01
Author
Dengiz, Çağatay
Metadata
Show full item record
This work is licensed under a
Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License
.
Item Usage Stats
148
views
0
downloads
Cite This
A series of new push-pull chromophores were synthesized in moderate to very high yields (65%-97%) by treating TCNE and TCNQ with alkynes substituted by electron-rich diethylaniline and polycyclic aromatic hydrocarbons. Some of the chromophores exhibit strong intramolecular charge-transfer bands in the near-1R region with lambda(max). values between 695 and 749 nm. With the help of experimental and theoretical analysis, it is concluded that the trend in lambda(max) values is affected by PAH substituents sterically, not electronically. Steric constraints led to the increased dihedral angles, reducing conjugation efficiencies. The absorption properties of push-pull compounds have been investigated in solvents possessing different polarities. All chromophores exhibited positive solvatochromism. As an additional proof of efficient charge-transfer in push-pull chromophores, quinoid character (dr) values were predicted using calculated bond lengths. Remarkably, substantial dr values (0.045-0.049) were predicted for donor diethylaniline rings in all compounds. The effects of various polycyclic aromatic hydrocarbons on optical and nonlinear optical properties were also studied by computational methods. Several parameters, such as band gaps, Mulliken electronegativity, chemical hardness and softness, dipole moments, average polarizability, first hyperpolarizability, were predicted for chromophores at the B3LYP/6-31+ +G(d,p) level of theory. The predicted first hyperpolarizability beta((tot)) values vary between 198 to 538 x 10(-30) esu for the reported push-pull chromophores in this study. The highest predicted beta((tot)) value in this study is 537.842 x 10(-30) esu, 8150 times larger than the predicted beta((tot)) value of benchmark NLO material urea, suggests possible utilization of these chromophores in NLO devices. The charge-transfer character of the synthesized structures was further confirmed by HOMO-LUMO depictions and electrostatic potential maps.
URI
https://hdl.handle.net/11511/94542
Journal
TURKISH JOURNAL OF CHEMISTRY
DOI
https://doi.org/10.3906/kim-2102-22
Collections
Department of Chemistry, Article
Suggestions
OpenMETU
Core
Enantioselective synthesis of 2-(2-arylcyclopropyl)glycines: Conformationally restricted homophenylalanine analogs
Demir, Ayhan Sıtkı; Sesenoglu, O; Ulku, D; Arici, C (Wiley, 2004-01-01)
Starting from simple aromatic aldehydes and acetylfuran, (E)-1-(furan-2-yl)-3-arylprop-2-en-1-ones (2) were synthesized in high yields. Cyclopropanation of the C=C bond with trimethylsulfoxonium iodide (Me3SO+I-) furnished (furan-2-yl)(2-arylcyclopropyl)methanones 3 in 90-97% yields. Selective conversion of cyclopropyl ketones to their (E)- and (Z)-oxime ethers 5 and oxazaborolidine-catalyzed stercoselective reduction of the C-N bond followed by separation of the formed diastereoisomers, furnished (2-arylcy...
Facile synthesis of novel 7-aminofuro- and 7-aminothieno[2,3-d]pyridazin-4(5H)-one and 4-aminophthalazin-1(2H)-ones
Koza, Gani; Keskin, Selbi; Ozer, Merve Sinem; Cengiz, Betul; ŞAHİN, Ertan; Balcı, Metin (2013-01-07)
We hereby report the synthesis of a novel class of compounds, 7-aminofuro- and 7-aminothieno[2,3-d]pyridazin-4(5H)-one and 4-aminophthalazin-1(2H)-ones starting from methyl 2-(2-methoxy-2-oxoethyl)furan- and thiophene-3-carboxylate and methyl 2-(2-methoxy-2-oxoethyl)benzoate. The ester functionalities connected directly to the aromatic ring were regiospecifically converted to the acid, whereas methylene groups were oxidized to the corresponding ketoesters. Reaction of the ketoesters with hydrazine provided ...
Viscoelastic properties of reactive and non-reactive styrene-maleic anhydride olefinic blends
Bayram, G; Yılmazer, Ülkü; Xanthos, M (2000-05-11)
Reactive blends of styrene-maleic anhydride (SMAH) with polyethylene/methyl acrylate/glycidyl methacrylate (PE-F) and non-reactive blends of SMAH with polyethylene/methyl acrylate (PE-NF) were produced and characterized in terms of morphology and viscoelastic properties in order to understand the reaction characteristics between anhydride/epoxy functional groups. Storage modulus, G', loss modulus, G " and complex viscosity, eta* of reactive blends at 25 % and 50 % PE-F were higher than those of non-reactive...
Electrochemical and optical properties of novel terthienyl based azobenzene, coumarine and fluorescein containing polymers: Multicolored electrochromic polymers
Yigit, Deniz; Udum, Yasemin Arslan; GÜLLÜ, Mustafa; Toppare, Levent Kamil (Elsevier BV, 2014-01-01)
Three electroactive terthienyl based monomers, namely 1-phenyl-2-[4-(2,2':5',2 ''-terthien-3'-ylmethoxy)phenyl]diazene (TTAz), 4-(2,2':5',2 ''-terthien-3'-ylmethoxy)-2H-chromen-2-one (TTCo) and methyl 2-[3-oxo-6-(2,2':5',2 ''-terthien-3'-ylmethoxy)-3H-xanthen-9-yl] benzoate (TTFlo), were synthesized with good yields and their conducting polymers were electrochemically prepared on ITO electrode surfaces. The effect of chromophore type on electrochemical and optical properties of the polymers was investigated...
Polyaniline: synthesis characterization solution properties and composites
Yılmaz, Faris; Küçükyavuz, Zuhal; Department of Polymer Science and Technology (2007)
Polyaniline was chemically synthesized at three different temperatures of 25, 0, and -25oC, by oxidative polymerization with ammonium peroxidisulfate at equimolar of aniline to oxidant ratio and 1M HCl. The resulted polyaniline was in a powder form which was characterized by several techniques such as: electrical conductivity, elemental analysis, thermal analysis, wide-angle X-Ray diffraction, and scanning electron microscope. The solution properties of the reduced polymer were studied by viscometry, static...
Citation Formats
IEEE
ACM
APA
CHICAGO
MLA
BibTeX
Ç. Dengiz, “Polycyclic aromatic hydrocarbon-substituted push-pull chromophores: an investigation of optoelectronic and nonlinear optical properties using experimental and theoretical approaches,”
TURKISH JOURNAL OF CHEMISTRY
, vol. 45, no. 5, pp. 1375–1424, 2021, Accessed: 00, 2021. [Online]. Available: https://hdl.handle.net/11511/94542.