New bridged oligofuran for optoelectronic applications

Tibaoui, T.; Ayachi, S.; Chemek, Mourad; Alimi, K.

doi:10.1016/j.saa.2015.01.073

Cited by 4 publications

(2 citation statements)

References 28 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Because of its synthetic accessibility, one of the most common building blocks used in the development of organic semiconducting materials is the sulfur-containing heterocycle thiophene [30]. Oligofurans have also emerged as promising building blocks for self-assembled organic semiconducting materials [30][31][32][33][34][35][36][37][38][39]. The presence of the oxygen atom in place of a sulfur atom in the five-membered aromatic heterocyclic rings gives rise to electron-rich conjugated systems exhibiting a tighter solid-state packing and even greater rigidity when compared to those of thiophene analogues [38,40,41].…”

Section: Introductionmentioning

confidence: 99%

A Raman Spectroscopic and Computational Study of New Aromatic Pyrimidine-Based Halogen Bond Acceptors

et al. 2019

View full text Add to dashboard Cite

Two new aromatic pyrimidine-based derivatives designed specifically for halogen bond directed self-assembly are investigated through a combination of high-resolution Raman spectroscopy, X-ray crystallography, and computational quantum chemistry. The vibrational frequencies of these new molecular building blocks, pyrimidine capped with furan (PrmF) and thiophene (PrmT), are compared to those previously assigned for pyrimidine (Prm). The modifications affect only a select few of the normal modes of Prm, most noticeably its signature ring breathing mode, ν1. Structural analyses afforded by X-ray crystallography, and computed interaction energies from density functional theory computations indicate that, although weak hydrogen bonding (C–H···O or C–H···N interactions) is present in these pyrimidine-based solid-state co-crystals, halogen bonding and π-stacking interactions play more dominant roles in driving their molecular-assembly.

show abstract

Section: Introductionmentioning

confidence: 99%

A Raman Spectroscopic and Computational Study of New Aromatic Pyrimidine-Based Halogen Bond Acceptors

et al. 2019

View full text Add to dashboard Cite

show abstract

“…More recently, studies have emerged focusing on their close analogues, oligofurans. ,,− The presence of an oxygen atom instead of a sulfur atom in these five-membered aromatic heterocycles gives rise to electron-rich conjugated systems exhibiting tighter solid-state packing and greater rigidity when compared to those of thiophene analogues. , In-depth analysis of oligofurans and oligothiophenes indicates that furan has a smaller molecular size than thiophene. This is a consequence of the greater atomic radius of sulfur compared to that of oxygen, 180 and 152 pm, respectively .…”

Section: Introductionmentioning

confidence: 99%

Characterization of Furan- and Thiophene-Containing Bispyridyl Oligomers via Spectroscopic, Electrochemical, and TD-DFT Methods

et al. 2019

View full text Add to dashboard Cite

The study of π-conjugated oligomers has garnered significant interest because of their use in organic optoelectronic devices, such as organic light-emitting diodes or organic field-effect transistors. Herein, we varied the inner heterocyclic units of pyridyl (Pyr)-capped π-conjugated oligomers consisting of furan (F) and thiophene (T) subunits to afford homomeric (Pyr 2 F 3 and Pyr 2 T 3 ) and heteromeric (Pyr 2 F 2 T and Pyr 2 T 2 F) molecules as applicable semiconducting building blocks. The oligomers were synthesized, and their solution- and solid-state spectroscopic properties were characterized. Compared to their thiophene congeners, oligomers with furans directly attached to the pyridyl moieties (Pyr 2 F 3 and Pyr 2 F 2 T) gave rise to larger solution-state quantum yields and optical band gaps. Oligomers possessing a central furan subunit (Pyr 2 F 3 and Pyr 2 T 2 F), on the other hand, were found to be nearly nonemissive in the solid state, which is attributed to nonradiative decay likely caused by π–π stacking interactions. Unlike the Pyr 2 T 2 F hybrid oligomer, Pyr 2 F 2 T exhibited not only a comparatively high solution-state quantum yield (7%) but also the brightest solid-state quantum yield emission (5%) and photostability (98%) when evaluated under ambient conditions. Density functional theory (DFT) computations support these trends, indicating that the largest HOMO–LUMO energy gaps and optical band gaps are possessed by Pyr 2 F 3 and Pyr 2 F 2 T while those of Pyr 2 T 2 F and Pyr 2 T 3 are the lowest among the oligomers considered here (i.e., Pyr 2 F 3 > Pyr 2 F 2 T > Pyr 2 T 2 F > Pyr 2 T 3 ). These results suggest that hybrid furan–thiophene oligomerslike that of Pyr 2 F 2 Tcould serve as viable building blocks for optoelectronic devices, while possessing the positive attributes of both individual heterocycles in a synergistic manner.

show abstract

Molecular structure–optical property relationships of 1,3-bis (4-methoxyphenyl) prop-2-en-1-one: A DFT and TD-DFT investigation

Ghomrasni

Aribi

Ayachi

et al. 2015

Journal of Physics and Chemistry of Solids

View full text Add to dashboard Cite

New bridged oligofuran for optoelectronic applications

Cited by 4 publications

References 28 publications

A Raman Spectroscopic and Computational Study of New Aromatic Pyrimidine-Based Halogen Bond Acceptors

A Raman Spectroscopic and Computational Study of New Aromatic Pyrimidine-Based Halogen Bond Acceptors

Characterization of Furan- and Thiophene-Containing Bispyridyl Oligomers via Spectroscopic, Electrochemical, and TD-DFT Methods

Molecular structure–optical property relationships of 1,3-bis (4-methoxyphenyl) prop-2-en-1-one: A DFT and TD-DFT investigation

Contact Info

Product

Resources

About