Electronic Structures and Spectroscopic Characters of Modified Oligo(alkylenedioxypyrrole)

Abstract

Polyalkylenedioxypyrrole (PADOP) exhibited an excellent conductivity experimentally. A series of oligomers for the electron-rich monomer alkylenedioxypyrrole (ADOP) were designed in order to study properties of PADOP. The structures of these oligomers were optimized using density function theory (DFT) at B3LYP/6-31G(d) level. The energy gaps and thermal stabilities of the oligomers were decreased when the chain lengths were increased. These properties were also decreased with the enlargement of the neighboring substituted rings. The 13 C nuclear magnetic resonance (NMR) spectra and nucleus independent chemical shifts (NICS) of the oligomers were calculated at B3LYP/6-31G(d) level. The chemical shifts at δ 96.1 of the linking carbon atoms in the dimer of 3,4-methylenedioxypyrrole (MDOP) were moved downfield relative to those at δ 89.5 of the same carbon atoms in the monomer of MDOP. The aromaticity of the central pyrrole ring in the oligomers is improved with the enlargement of the neighboring substituted rings.

Effectiveness of alternating mammography and magnetic resonance imaging for screening women with deleterious BRCA mutations at high risk of breast cancer

“…Up to now, the family of EDOT analogs includes (1) ring‐size variations, 3,4‐methylenedioxythiophene (MDOT), 3,4‐propylenedioxythiophene (PDOT), and 3,4‐butylenedioxythiophene (BDOT);12, 13 (2) sulfur analogs, 3,4‐methylenedithiathiophene (MDTT), 3,4‐ethylenedithiathiophene (EDTT), EDTT‐R (R = Br, CH 2 OH etc. ), 3,4‐propylenedithiathiophene (PDTT), and thieno[3,4‐ b ]‐1,4‐oxathiane (EOTT);14–18 (3) selenium analogs, 3,4‐ethylenedioxyselenophene (EDOS), 3,4‐propylenedioxyselenophene (PDOS), PEDOS‐R 2 (R 2 = C n H 2 n +1 , n = 4, 6, 10), 3,4‐ethylenedithioselenophene (EDTS), seleno[3,4‐ b ]‐1,4‐oxathiane (EOTS), and 3,4‐ethylenediselenathiophene (EDST);19–25 (4) nitrous analogs, 3,4‐methylenedioxypyrrole (MDOPy), 3,4‐ethylenedioxypyrrole (EDOPy), 3,4‐propylenedioxypyrrole (PDOPy), 3,4‐butylenedioxypyrrole (BDOPy), 3,4‐methylenedithiopyrrole (MDTPy), and 3,4‐ethylenedithiopyrrole (EDTPy);26–29 (5) phosphorous analog, 3,4‐ethylenedithiaphosphole (EDPP);30 (6) oxygenic analogs, 3,4‐ethylendithiafurane (EDTF), 3,4‐ethylenedioxyfuran (EDOF), and 3,4‐dihydro‐2 H ‐thieno[3,4‐ b ]pyran (EDTP);31–33 (7) telluric analog, 3,4‐ethylenedioxytellurophene (EDOTe) as a predicted structure based on 3,4‐dimethoxytellurophene (DMOTe) 34. Structures of the above are summarized in Scheme .…”

Poly(thieno[3,4-b]-1,4-oxathiane) and poly(3,4-ethylenedioxythiophene-co-thieno[3,4-b]-1,4-oxathiane)/poly(styrene sulfonic sodium): Preparation, characterization, and optoelectronic performance

“…Therefore, many research groups have paid attention to the development of EDOT analogs which can be obtained via changing the heteroatom in the conjugated backbone or peripheral ring of EDOT . Among them, sulfur analogs, selenium analogs, and nitrous analogs have been developed rapidly in recent years. The selenium analog poly(3,4‐ethylenedioxyselenophene) and the derivatives were mainly developed by Bendikov et al, and they have more easily polarized and lower aromatized selenophene ring.…”