PMID- 31315394
OWN - NLM
STAT- PubMed-not-MEDLINE
LR  - 20190923
IS  - 1520-6904 (Electronic)
IS  - 0022-3263 (Linking)
VI  - 84
IP  - 16
DP  - 2019 Aug 16
TI  - Synthesis of Bis([2,2'-bithiophen]-5-yl)-Substituted Oligothiadiazoles: Effect of 
      the Number of Acceptor Units on Electrochemical and Spectroscopic Properties.
PG  - 10040-10049
LID - 10.1021/acs.joc.9b01216 [doi]
AB  - 1,3,4-Thiadiazole, 2,2'-bi(1,3,4-thiadiazole), 2,2':5',2''-ter(1,3,4-thiadiazole), 
      and 2,2':5',2'':5'',2'''-quater(1,3,4-thiadiazole) symmetrically disubstituted with 
      3-alkyl-(2,2'-bithiophen)-5-yl were synthesized by new procedures using readily 
      available ethyl 3-alkyl-(2,2'-bithiophene)-5-carboxylate as a convenient 
      substrate. These new compounds with a fixed number of donor rings and increasing 
      number of acceptor rings showed very interesting, tunable redox properties. In 
      particular, they exhibited electron affinities (EAs) ranging from -3.06 to -3.83 
      eV, reaching EA values desired for air-operating n-type organic semiconductors. 
      Their electrochemically determined ionization potentials were only moderately 
      dependent on the number of thiadiazole rings, varying from 5.83 to 6.01 eV. 
      Emission spectra of these compounds could also be tuned in a wide range (from 470 
      to 600 nm). Spectroscopic and electrochemical data were confirmed by density 
      functional theory calculations demonstrating full consistency.
FAU - Kostyuchenko, Anastasia S
AU  - Kostyuchenko AS
AD  - Laboratory of New Organic Materials , Omsk State Technical University , Mira ave. 
      11 , Omsk 644050 , Russian Federation.
FAU - Kurowska, Aleksandra
AU  - Kurowska A
AD  - Faculty of Chemistry , Silesian University of Technology , Marcina Strzody 9 , 
      Gliwice 44-100 , Poland.
FAU - Zassowski, Pawel
AU  - Zassowski P
AD  - Faculty of Chemistry , Silesian University of Technology , Marcina Strzody 9 , 
      Gliwice 44-100 , Poland.
FAU - Zheleznova, Tatyana Yu
AU  - Zheleznova TY
AD  - Department of Organic Chemistry , Omsk F. M. Dostoevsky State University , Mira 
      ave. 55A , Omsk 644077 , Russian Federation.
FAU - Ulyankin, Evgeny B
AU  - Ulyankin EB
AD  - Department of Organic Chemistry , Omsk F. M. Dostoevsky State University , Mira 
      ave. 55A , Omsk 644077 , Russian Federation.
FAU - Domagala, Wojciech
AU  - Domagala W
AUID- ORCID: 0000-0002-8885-729X
AD  - Faculty of Chemistry , Silesian University of Technology , Marcina Strzody 9 , 
      Gliwice 44-100 , Poland.
FAU - Pron, Adam
AU  - Pron A
AD  - Faculty of Chemistry , Warsaw University of Technology , Noakowskiego 3 , 
      Warszawa 00-664 , Poland.
FAU - Fisyuk, Alexander S
AU  - Fisyuk AS
AUID- ORCID: 0000-0001-6191-9297
AD  - Laboratory of New Organic Materials , Omsk State Technical University , Mira ave. 
      11 , Omsk 644050 , Russian Federation.
LA  - eng
PT  - Journal Article
DEP - 20190801
PL  - United States
TA  - J Org Chem
JT  - The Journal of organic chemistry
JID - 2985193R
SB  - IM
EDAT- 2019/07/19 06:00
MHDA- 2019/07/19 06:01
CRDT- 2019/07/19 06:00
PHST- 2019/07/19 06:00 [pubmed]
PHST- 2019/07/19 06:01 [medline]
PHST- 2019/07/19 06:00 [entrez]
AID - 10.1021/acs.joc.9b01216 [doi]
PST - ppublish
SO  - J Org Chem. 2019 Aug 16;84(16):10040-10049. doi: 10.1021/acs.joc.9b01216. Epub 
      2019 Aug 1.