Abstract
Independent of the substrate structure and reaction conditions, 3-amino-2-cyanothioacrylamides, which contain two active electrophilic centers, were shown to interact with various active halo methylene compounds under mild conditions to afford 5-acyl-2-amino-3-cyanothiophenes as the only products. A series of new polyfunctional thiophene derivatives with a rare combination of functionalities were synthesized, and their photophysical properties were experimentally and computationally investigated. The calculated electronic characteristics of the ground and excited states were compared to the experimental results, which provided a good understanding of the relationship between the optoelectronic properties and the molecular structures. After absorption of light quanta, the systems populate an intramolecular charge-transfer (ICT) Franck–Condon state, and emission occurs from a twisted ICT minimum.
| Original language | English |
|---|---|
| Pages (from-to) | 2410-2425 |
| Number of pages | 16 |
| Journal | Chemistry - An Asian Journal |
| Volume | 12 |
| Issue number | 18 |
| DOIs | |
| Publication status | Published - 19 Sep 2017 |
| Externally published | Yes |
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Keywords
- charge transfer
- cyclization
- fluorescence
- solvatochromism
- sulfur heterocycles
ASJC Scopus subject areas
- Biochemistry
- Organic Chemistry
Cite this
Synthesis of 5-Acyl-2-Amino-3-Cyanothiophenes : Chemistry and Fluorescent Properties. / Lugovik, Kseniya I.; Eltyshev, Alexander K.; Benassi, Enrico; Belskaya, Nataliya P.
In: Chemistry - An Asian Journal, Vol. 12, No. 18, 19.09.2017, p. 2410-2425.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Synthesis of 5-Acyl-2-Amino-3-Cyanothiophenes
T2 - Chemistry and Fluorescent Properties
AU - Lugovik, Kseniya I.
AU - Eltyshev, Alexander K.
AU - Benassi, Enrico
AU - Belskaya, Nataliya P.
PY - 2017/9/19
Y1 - 2017/9/19
N2 - Independent of the substrate structure and reaction conditions, 3-amino-2-cyanothioacrylamides, which contain two active electrophilic centers, were shown to interact with various active halo methylene compounds under mild conditions to afford 5-acyl-2-amino-3-cyanothiophenes as the only products. A series of new polyfunctional thiophene derivatives with a rare combination of functionalities were synthesized, and their photophysical properties were experimentally and computationally investigated. The calculated electronic characteristics of the ground and excited states were compared to the experimental results, which provided a good understanding of the relationship between the optoelectronic properties and the molecular structures. After absorption of light quanta, the systems populate an intramolecular charge-transfer (ICT) Franck–Condon state, and emission occurs from a twisted ICT minimum.
AB - Independent of the substrate structure and reaction conditions, 3-amino-2-cyanothioacrylamides, which contain two active electrophilic centers, were shown to interact with various active halo methylene compounds under mild conditions to afford 5-acyl-2-amino-3-cyanothiophenes as the only products. A series of new polyfunctional thiophene derivatives with a rare combination of functionalities were synthesized, and their photophysical properties were experimentally and computationally investigated. The calculated electronic characteristics of the ground and excited states were compared to the experimental results, which provided a good understanding of the relationship between the optoelectronic properties and the molecular structures. After absorption of light quanta, the systems populate an intramolecular charge-transfer (ICT) Franck–Condon state, and emission occurs from a twisted ICT minimum.
KW - charge transfer
KW - cyclization
KW - fluorescence
KW - solvatochromism
KW - sulfur heterocycles
UR - http://www.scopus.com/inward/record.url?scp=85027855322&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=85027855322&partnerID=8YFLogxK
U2 - 10.1002/asia.201700721
DO - 10.1002/asia.201700721
M3 - Article
VL - 12
SP - 2410
EP - 2425
JO - Chemistry - An Asian Journal
JF - Chemistry - An Asian Journal
SN - 1861-4728
IS - 18
ER -