FRINK Linked Data Fragments server

Matches in SemOpenAlex for { <https://semopenalex.org/work/W2079010372> ?p ?o ?g. }

• W2079010372 endingPage "14407" @default.
• W2079010372 startingPage "14397" @default.
• W2079010372 abstract "The electronic and optical properties of 2,6-dialkyl and 2,6-bis(5-alkyl-2-thienyl) derivatives of the fused-ring systems 4H-cyclopenta[2,1-b:3,4-b′]bithiophene, 4,4-di-n-hexyl-4H-cyclopenta[2,1-b:3,4-b′]bithiophene, 4H-cyclopenta[2,1-b:3,4-b′]bithiophene-4-one, 4-alkyl and 4-aryldithieno[3,2-b:2′,3′-d]pyrrole, 4-phenyldithieno[3,2-b:2′,3′-d]phosphole, 4-phenyldithieno[3,2-b:2′,3′-d]phosphole 4-oxide, dithieno[3,2-b:2′,3′-d]thiophene, dithieno[3,2-b:2′,3′-d]thiophene 4-oxide, and dithieno[3,2-b:2′,3′-d]thiophene 4,4-dioxide have been compared to those of the analogous unbridged 5,5′-substituted 2,2′-bithiophene derivatives using electrochemistry, UV−visible absorption and emission spectroscopy, and DFT and TD-DFT calculations. The planarization in the fused-ring compounds means that the methylene-bridged cyclopentabithiophenes are more readily oxidized than their unbridged bithiophene analogues. In each case, the bridging group (X) lies on a nodal plane of the HOMO; accordingly, within each series of fused-ring compounds, electrochemical oxidation potentials and calculated ionization potentials depend primarily on the inductive donor/acceptor strength of the bridging group. On the other hand, significant LUMO coefficients can be found on X groups with π-donor or acceptor properties; accordingly, the electrochemical reduction potentials, calculated electron affinities, and the energies of the HOMO→LUMO optical transitions depend on both inductive and mesomeric donor and acceptor strengths. In particular, within the 2,6-bis(5-alkyl-2-thienyl) series, increasingly electron-withdrawing bridging groups lead to a bathochromic shift and weakening of the low-energy absorption band relative to that of methylene- or π-donor-bridged examples and also to a loss of vibronic structure, with the compound that has the strongest π-accepting bridge of those examined (X = CO) showing a particularly low-energy and weak band. The fluorescence of acceptor-bridged compounds exhibits greater Stokes shifts and a loss of vibronic structure relative to those of methylene- or π-donor-bridged analogues, with the carbonyl-bridged derivative showing no observable fluoresence. These results can be related to increasing localization of the LUMO on the core and toward the bridging group, leading to increased charge-transfer character for the first excited state. The radical cations of some examples have been generated by chemical oxidation and investigated using visible-NIR and ESR spectroscopy and DFT and TD-DFT calculations. The absorption spectra of the radical cations of the 2,6-bis(5-alkyl-2-thienyl) compounds are generally similar to those previously reported for quaterthiophene derivatives, while the hyperfine couplings obtained from ESR spectra are consistent with delocalization of the unpaired electron over both the core and terminal thienyl rings of the π system." @default.
• W2079010372 created "2016-06-24" @default.
• W2079010372 creator A5014392016 @default.
• W2079010372 creator A5021231690 @default.
• W2079010372 creator A5028684191 @default.
• W2079010372 creator A5045853606 @default.
• W2079010372 creator A5050152527 @default.
• W2079010372 creator A5067812308 @default.
• W2079010372 creator A5071412765 @default.
• W2079010372 creator A5076609099 @default.
• W2079010372 date "2010-04-16" @default.
• W2079010372 modified "2023-09-27" @default.
• W2079010372 title "Electronic and Optical Properties of 4<i>H</i>-Cyclopenta[2,1-<i>b</i>:3,4-<i>b′</i>]bithiophene Derivatives and Their 4-Heteroatom-Substituted Analogues: A Joint Theoretical and Experimental Comparison" @default.
• W2079010372 cites W1946922275 @default.
• W2079010372 cites W1967026714 @default.
• W2079010372 cites W1975021826 @default.
• W2079010372 cites W1975238618 @default.
• W2079010372 cites W1975530723 @default.
• W2079010372 cites W1976888797 @default.
• W2079010372 cites W1976952715 @default.
• W2079010372 cites W1984154450 @default.
• W2079010372 cites W1985368291 @default.
• W2079010372 cites W1992223836 @default.
• W2079010372 cites W1992467601 @default.
• W2079010372 cites W1993181585 @default.
• W2079010372 cites W1995060095 @default.
• W2079010372 cites W1995322248 @default.
• W2079010372 cites W1997593366 @default.
• W2079010372 cites W2001176028 @default.
• W2079010372 cites W2002815086 @default.
• W2079010372 cites W2004776321 @default.
• W2079010372 cites W2014165099 @default.
• W2079010372 cites W2015349740 @default.
• W2079010372 cites W2016943360 @default.
• W2079010372 cites W2017931317 @default.
• W2079010372 cites W2018094686 @default.
• W2079010372 cites W2020126415 @default.
• W2079010372 cites W2020602731 @default.
• W2079010372 cites W2021644247 @default.
• W2079010372 cites W2023445475 @default.
• W2079010372 cites W2023596756 @default.
• W2079010372 cites W2026195409 @default.
• W2079010372 cites W2029199009 @default.
• W2079010372 cites W2030763137 @default.
• W2079010372 cites W2031904250 @default.
• W2079010372 cites W2033432852 @default.
• W2079010372 cites W2038499273 @default.
• W2079010372 cites W2039610275 @default.
• W2079010372 cites W2041504070 @default.
• W2079010372 cites W2043007197 @default.
• W2079010372 cites W2043050949 @default.
• W2079010372 cites W2043703221 @default.
• W2079010372 cites W2045808316 @default.
• W2079010372 cites W2046603144 @default.
• W2079010372 cites W2048908694 @default.
• W2079010372 cites W2049642802 @default.
• W2079010372 cites W2049788859 @default.
• W2079010372 cites W2051233927 @default.
• W2079010372 cites W2051239237 @default.
• W2079010372 cites W2051241647 @default.
• W2079010372 cites W2055499045 @default.
• W2079010372 cites W2056215645 @default.
• W2079010372 cites W2058191604 @default.
• W2079010372 cites W2058980730 @default.
• W2079010372 cites W2060026323 @default.
• W2079010372 cites W2061445187 @default.
• W2079010372 cites W2062683818 @default.
• W2079010372 cites W2062959230 @default.
• W2079010372 cites W2063074480 @default.
• W2079010372 cites W2065720971 @default.
• W2079010372 cites W2065735841 @default.
• W2079010372 cites W2065844946 @default.
• W2079010372 cites W2069917295 @default.
• W2079010372 cites W2070666067 @default.
• W2079010372 cites W2070905703 @default.
• W2079010372 cites W2072110781 @default.
• W2079010372 cites W2075580333 @default.
• W2079010372 cites W2076992071 @default.
• W2079010372 cites W2081245148 @default.
• W2079010372 cites W2083386084 @default.
• W2079010372 cites W2084077065 @default.
• W2079010372 cites W2084975965 @default.
• W2079010372 cites W2088778204 @default.
• W2079010372 cites W2090401462 @default.
• W2079010372 cites W2092026332 @default.
• W2079010372 cites W2092457617 @default.
• W2079010372 cites W2093018840 @default.
• W2079010372 cites W2093307651 @default.
• W2079010372 cites W2099557209 @default.
• W2079010372 cites W2101797469 @default.
• W2079010372 cites W2112453573 @default.
• W2079010372 cites W2115162744 @default.
• W2079010372 cites W2137733516 @default.
• W2079010372 cites W2137975664 @default.
• W2079010372 cites W2144573598 @default.
• W2079010372 cites W2148351384 @default.
• W2079010372 cites W2153385810 @default.
• W2079010372 cites W2160790360 @default.

• next