Org Lett
Department of Chemistry, University of California-Berkeley, Berkeley, California 94720-1460, USA.
Published: May 2003
[structure: see text] A series of bridged oligothiophenes have been synthesized. Their novel molecular architecture, comprising two oligothiophenes linked together by a bridge at one alpha-extremity and one binding group at the other alpha-extremity, is expected to improve their utility as electroactive surfactants for semiconducting nanoparticles or organic electronics.
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http://dx.doi.org/10.1021/ol034398q | DOI Listing |
Chem Sci
November 2023
Department of Chemistry, University of South Florida 4202 E. Fowler Avenue, CHE 205 Tampa FL 33620-5250 USA.
A series of oligothiophene bis(dioxolene) complexes, SQ-Th-SQ (SQ = = ½TpZn(3--butyl-orthosemiquinonate); Tp = tris(5-cumenyl-3-methylpyrazolyl)borate anion) have been synthesized, structurally characterized, and studied as a function of the number of thiophene bridging units, ( = 0-3) using a combination of variable-temperature (VT) electronic absorption and EPR spectroscopies, and VT magnetic susceptibility measurements. The thiophene bridge bond lengths determined by X-ray crystallography display dramatic differences across the SQ-Th-SQ series. Bridge bond deviation values (Σ||) display a progressive change in the nature of the bridge fragment bonding as the number of thiophene groups increases, with quinoidal bridge character for = 1 (SQ-Th-SQ) and biradical character with "aromatic" bridge bond lengths for = 3 (SQ-Th-SQ).
View Article and Find Full Text PDFJ Am Chem Soc
November 2023
Department of Chemistry, University of Toronto, Toronto, Ontario M5S 3H6, Canada.
Conjugated macromolecules have a rich history in chemistry, owing to their chemical arrangements that intertwine physical and electronic properties. The continuing study and application of these systems, however, necessitates the development of atomically precise models that bridge the gap between molecules, polymers, and/or their blends. One class of conjugated polymers that have facilitated the advancement of structure-property relationships is discrete, precision oligomers that have remained an outstanding synthetic challenge with only a handful of reported examples.
View Article and Find Full Text PDFACS Appl Mater Interfaces
September 2023
Department of Chemistry, University of Texas at San Antonio, One UTSA Circle, San Antonio, Texas 78249, United States.
A series of diblock oligomers containing oligothiophene (T, = 4, 5) and 4,7-di(thiophen-2-yl)benzo[][1,2,5]thiadizole (TBT) segments, functionalized with carboxylic acid anchoring groups, were prepared and anchored to mesoporous TiO films to study wavelength-dependent interfacial electron transfer mechanisms. Thin films of the surface-anchored diblock oligomers contained two absorption bands centered at 400 and 500 nm, corresponding to the T and TBT blocks, respectively. Pulsed-laser excitation of the oligomer-sensitized films yielded local excited-states that promoted electron injection into TiO.
View Article and Find Full Text PDFChemistry
May 2022
Institut für Organische Chemie, Universität Würzburg, Am Hubland, 97074, Würzburg, Germany.
A series of donor-acceptor (D-A) macrocyclic dyads consisting of an electron-poor perylene bisimide (PBI) π-scaffold bridged with electron-rich α-oligothiophenes bearing four, five, six and seven thiophene units between the two phenyl-imide substituents has been synthesized and characterized by steady-state UV/Vis absorption and fluorescence spectroscopy, cyclic and differential pulse voltammetry as well as transient absorption spectroscopy. Tying the oligothiophene strands in a conformationally fixed macrocyclic arrangement leads to a more rigid π-scaffold with vibronic fine structure in the respective absorption spectra. Electrochemical analysis disclosed charged state properties in solution which are strongly dependent on the degree of rigidification within the individual macrocycle.
View Article and Find Full Text PDFPhys Chem Chem Phys
November 2021
School of Physical Science and Technology, ShanghaiTech University, 201210 Shanghai, People's Republic of China.
Due to efficient intersystem crossing (ISC), combined with efficient non-radiative processes of the triplet excited state, oligothiophenes generally exhibit very weak photoluminescence. Phosphorus (P)-bridged terthiophenes (P-terThs) and phosphorus (P)-bridged bithiophenes (P-biThs) were synthesized. The diverse and well-defined P-chemistry has been applied to fine tune the photophysical properties of these materials.
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