Design and Theoretical Study of D–A–π–A Organic Sensitizers with [1,2,5]Thiadiazolo[3,4-c]pyridine, [1,2,5]Selenadiazolo[3,4-c]pyridine, and [1,2,5]Oxadiazolo[3,4-c]pyridine π Component
The study concerns molecular design and theoretical study of novel prospective organic sensitizers based on D–A–π–A concept. A modification of the concept (DA–π–A) and new ways for design of organic sensitizers are proposed. The study shows that π-block plays a key role for the wavelength shift in U...
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| Format: | Article |
| Language: | English |
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Wiley
2015-01-01
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| Series: | Journal of Chemistry |
| Online Access: | http://dx.doi.org/10.1155/2015/467593 |
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| author | O. I. Bolshakov M. A. Grishina A. Galushko V. A. Potemkin O. A. Rakitin |
| author_facet | O. I. Bolshakov M. A. Grishina A. Galushko V. A. Potemkin O. A. Rakitin |
| author_sort | O. I. Bolshakov |
| collection | DOAJ |
| description | The study concerns molecular design and theoretical study of novel prospective organic sensitizers based on D–A–π–A concept. A modification of the concept (DA–π–A) and new ways for design of organic sensitizers are proposed. The study shows that π-block plays a key role for the wavelength shift in UV-Vis spectra. An existence of element of higher periods in the π-block provides a noticeable bathochromic shift. The thienyl bridge in A-block provides a red shift with respect to phenyl bridge for [1,2,5]oxadiazolo[3,4-c]pyridines while the phenyl bridge provides a red shift with respect to thienyl bridge for [1,2,5]selenadiazolo[3,4-c]pyridines. The maximal wavelengths are observed for DA-blocks with aliphatic/alicyclic fragments we proposed. An influence of enthalpy of formation and polarity of DA-blocks on bathochromic shift is shown. The quantitative dependencies of wavelengths on the enthalpies and dipole moments are determined. The maximal oscillator strengths are observed for the planar DA-block. Therefore, the conditions for design of compounds possessing the maximal wavelengths and oscillator strengths are different: the latter presupposes the planar structure of DA-block while the first presupposes an existence of nonplanar aliphatic/alicyclic fragments. Thus, the further design of organic sensitizers should include some combination of these concepts. |
| format | Article |
| id | doaj-art-3e75ac237df34866bc46cc965c95f58b |
| institution | Kabale University |
| issn | 2090-9063 2090-9071 |
| language | English |
| publishDate | 2015-01-01 |
| publisher | Wiley |
| record_format | Article |
| series | Journal of Chemistry |
| spelling | doaj-art-3e75ac237df34866bc46cc965c95f58b2025-02-03T01:09:43ZengWileyJournal of Chemistry2090-90632090-90712015-01-01201510.1155/2015/467593467593Design and Theoretical Study of D–A–π–A Organic Sensitizers with [1,2,5]Thiadiazolo[3,4-c]pyridine, [1,2,5]Selenadiazolo[3,4-c]pyridine, and [1,2,5]Oxadiazolo[3,4-c]pyridine π ComponentO. I. Bolshakov0M. A. Grishina1A. Galushko2V. A. Potemkin3O. A. Rakitin4Nanotechnology Education and Research Center, South Ural State University, Lenina Avenue 76, Chelyabinsk 454080, RussiaSouth Ural State Medical University, Chelyabinsk 454092, RussiaNanotechnology Education and Research Center, South Ural State University, Lenina Avenue 76, Chelyabinsk 454080, RussiaNanotechnology Education and Research Center, South Ural State University, Lenina Avenue 76, Chelyabinsk 454080, RussiaNanotechnology Education and Research Center, South Ural State University, Lenina Avenue 76, Chelyabinsk 454080, RussiaThe study concerns molecular design and theoretical study of novel prospective organic sensitizers based on D–A–π–A concept. A modification of the concept (DA–π–A) and new ways for design of organic sensitizers are proposed. The study shows that π-block plays a key role for the wavelength shift in UV-Vis spectra. An existence of element of higher periods in the π-block provides a noticeable bathochromic shift. The thienyl bridge in A-block provides a red shift with respect to phenyl bridge for [1,2,5]oxadiazolo[3,4-c]pyridines while the phenyl bridge provides a red shift with respect to thienyl bridge for [1,2,5]selenadiazolo[3,4-c]pyridines. The maximal wavelengths are observed for DA-blocks with aliphatic/alicyclic fragments we proposed. An influence of enthalpy of formation and polarity of DA-blocks on bathochromic shift is shown. The quantitative dependencies of wavelengths on the enthalpies and dipole moments are determined. The maximal oscillator strengths are observed for the planar DA-block. Therefore, the conditions for design of compounds possessing the maximal wavelengths and oscillator strengths are different: the latter presupposes the planar structure of DA-block while the first presupposes an existence of nonplanar aliphatic/alicyclic fragments. Thus, the further design of organic sensitizers should include some combination of these concepts.http://dx.doi.org/10.1155/2015/467593 |
| spellingShingle | O. I. Bolshakov M. A. Grishina A. Galushko V. A. Potemkin O. A. Rakitin Design and Theoretical Study of D–A–π–A Organic Sensitizers with [1,2,5]Thiadiazolo[3,4-c]pyridine, [1,2,5]Selenadiazolo[3,4-c]pyridine, and [1,2,5]Oxadiazolo[3,4-c]pyridine π Component Journal of Chemistry |
| title | Design and Theoretical Study of D–A–π–A Organic Sensitizers with [1,2,5]Thiadiazolo[3,4-c]pyridine, [1,2,5]Selenadiazolo[3,4-c]pyridine, and [1,2,5]Oxadiazolo[3,4-c]pyridine π Component |
| title_full | Design and Theoretical Study of D–A–π–A Organic Sensitizers with [1,2,5]Thiadiazolo[3,4-c]pyridine, [1,2,5]Selenadiazolo[3,4-c]pyridine, and [1,2,5]Oxadiazolo[3,4-c]pyridine π Component |
| title_fullStr | Design and Theoretical Study of D–A–π–A Organic Sensitizers with [1,2,5]Thiadiazolo[3,4-c]pyridine, [1,2,5]Selenadiazolo[3,4-c]pyridine, and [1,2,5]Oxadiazolo[3,4-c]pyridine π Component |
| title_full_unstemmed | Design and Theoretical Study of D–A–π–A Organic Sensitizers with [1,2,5]Thiadiazolo[3,4-c]pyridine, [1,2,5]Selenadiazolo[3,4-c]pyridine, and [1,2,5]Oxadiazolo[3,4-c]pyridine π Component |
| title_short | Design and Theoretical Study of D–A–π–A Organic Sensitizers with [1,2,5]Thiadiazolo[3,4-c]pyridine, [1,2,5]Selenadiazolo[3,4-c]pyridine, and [1,2,5]Oxadiazolo[3,4-c]pyridine π Component |
| title_sort | design and theoretical study of d a π a organic sensitizers with 1 2 5 thiadiazolo 3 4 c pyridine 1 2 5 selenadiazolo 3 4 c pyridine and 1 2 5 oxadiazolo 3 4 c pyridine π component |
| url | http://dx.doi.org/10.1155/2015/467593 |
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