In this study, two new thieno[3,2-]thiophene-diketopyrrolopyrrole (DPP)-based polymers, poly{2,5-bis(2-dodecylhexadecyl)-3,6-bis(thieno[3,2-]thiophen-2-yl)pyrrolo[3,4-]pyrrole-1,4(2,5)-dione-alt-2, 2'-bithiophene} (PTTDPP-BT) and {2,5-bis(2-dodecylhexadecyl)-3,6-bis(thieno[3,2-]thiophen-2-yl) pyrrolo[3,4-]pyrrole-1,4(2,5)-dione--2,2'-selenophene} (PTTDPP-BSe), which contained bithiophene (BT) and biselenophene (BSe) units, respectively, were designed and synthesized. The introduction of BT and BSe units affected the optical, electrochemical, morphological, and charge transport properties of the polymers. Experimental results revealed that the frontier molecular orbital energy levels of PTTDPP-BT were slightly higher because of the relatively strong electron donating ability of the sulfur atom and the polymer also exhibited good solubility. The maximum mobility in the case of PTTDPP-BT at 250 °C was 0.068 cm² V s and that of PTTDPP-BSe was 0.029 cm² V s (at 200 °C).
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http://dx.doi.org/10.1166/jnn.2019.17024 | DOI Listing |
Inorg Chem
November 2020
Istituto di Chimica dei Composti Organometallici, Via Madonna del Piano 10, 50019 Sesto Fiorentino, Italy.
The bicyclic ditopic linker 2,2'-biselenophene-5,5'-dicarboxylic acid (), specifically designed for metal-organic framework (MOF) construction, has been synthesized in good yield and fully characterized. The corresponding zirconium MOF (Zr-MOF) [ZrO(OH)(SpSp)Cl] (; where missing linkers are replaced by chloride anions as shown by X-ray fluorescence and elemental analysis) is isostructural with its bithiophene and bithiazole analogues. Starting from , an extension of the biselenophene-based Zr-MOF family has been successfully achieved, exploiting the structural analogy of the five-membered heterocycles selenophene, thiophene, and thiazole.
View Article and Find Full Text PDFJ Nanosci Nanotechnol
October 2019
Department of Chemistry and Chemistry Institute for Functional Materials, Pusan National University, Busan 609-735, Republic of Korea.
In this study, two new thieno[3,2-]thiophene-diketopyrrolopyrrole (DPP)-based polymers, poly{2,5-bis(2-dodecylhexadecyl)-3,6-bis(thieno[3,2-]thiophen-2-yl)pyrrolo[3,4-]pyrrole-1,4(2,5)-dione-alt-2, 2'-bithiophene} (PTTDPP-BT) and {2,5-bis(2-dodecylhexadecyl)-3,6-bis(thieno[3,2-]thiophen-2-yl) pyrrolo[3,4-]pyrrole-1,4(2,5)-dione--2,2'-selenophene} (PTTDPP-BSe), which contained bithiophene (BT) and biselenophene (BSe) units, respectively, were designed and synthesized. The introduction of BT and BSe units affected the optical, electrochemical, morphological, and charge transport properties of the polymers. Experimental results revealed that the frontier molecular orbital energy levels of PTTDPP-BT were slightly higher because of the relatively strong electron donating ability of the sulfur atom and the polymer also exhibited good solubility.
View Article and Find Full Text PDFACS Appl Mater Interfaces
March 2019
Center for Emergent Functional Matter Science , National Chiao Tung University , 1001 University Road, Hsinchu 30010 , Taiwan.
In this research, we developed six new selenophene-incorporated naphthobisthiadiazole-based donor-acceptor polymers PNT2Th2Se-OD, PNT2Se2Th-OD, PNT4Se-OD, PNT2Th2Se-DT, PNT2Se2Th-DT, and PNT4Se-DT. The structure-property relationships have been systematically established through the comparison of their structural variations: (1) isomeric biselenophene/bithiophene arrangement between PNT2Th2Se and PNT2Se2Th polymers, (2) biselenophene/bithiophene and quarterselenophene donor units between PNT2Th2Se/PNT2Se2Th and PNT4Se polymers, and (3) side-chain modification between the 2-octyldodecylthiophene (OD)- and 2-decyltetradecyl (DT)-series polymers. The incorporation of selenophene units in the copolymers induces stronger charge transfer to improve the light-harvesting capability while maintaining the strong intermolecular interactions to preserve the intrinsic crystallinity for high carrier mobility.
View Article and Find Full Text PDFJ Phys Chem A
November 2014
Department of Chemistry, University of Basel, St. Johanns-Ring 19 and Klingelbergstrasse 80, CH-4056 Basel, Switzerland.
A series of selenophenes with redox-active amine end-capping groups was synthesized and investigated. A combination of cyclic voltammetry, optical absorption, EPR spectroscopy, and quantum-chemical calculations based on Kohn-Sham density functional theory was used to explore charge delocalization in the monocationic mixed-valence forms of these selenophenes, and the results were compared to those obtained from analogous studies of structurally identical thiophenes. The striking finding is that the comproportionation constant (Kc) for the experimentally investigated biselenophene is more than 2 orders of magnitude lower than for its bithiophene counterpart (in CH3CN with 0.
View Article and Find Full Text PDFJ Chem Theory Comput
September 2014
Department of Chemistry, Texas A&M University , College Station, Texas 77842, United States.
The utility of π-conjugated oligomers and polymers continues to grow, and oligofurans, oligothiophenes, and oligoselenophenes have shown great promise in the context of organic electronic materials. Vital to the performance of these materials is the maintenance of planarity along the conjugated backbone. Consequently, there has been a great deal of work modeling the torsional behavior of these prototypical components of conjugated organic materials both in the gas and condensed phases.
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