Synthesis and optoelectronic properties of benzodithiophene-based conjugated polymers with hydrogen bonding nucleobase side chain functionality

2020 ◽  
Vol 11 (36) ◽  
pp. 5735-5749
Author(s):  
Sina Sabury ◽  
Tyler J. Adams ◽  
Margaret Kocherga ◽  
S. Michael Kilbey ◽  
Michael G. Walter

Nucleobase functionalities in conjugated, alternating copolymers participate in interbase hydrogen bonding, which promotes molecular assembly and organization in thin films and enhances optical and electronic properties.

2018 ◽  
Vol 115 (11) ◽  
pp. 2699-2704 ◽  
Author(s):  
Dominic Raithel ◽  
Lena Simine ◽  
Sebastian Pickel ◽  
Konstantin Schötz ◽  
Fabian Panzer ◽  
...  

The backbone conformation of conjugated polymers affects, to a large extent, their optical and electronic properties. The usually flexible substituents provide solubility and influence the packing behavior of conjugated polymers in films or in bad solvents. However, the role of the side chains in determining and potentially controlling the backbone conformation, and thus the optical and electronic properties on the single polymer level, is currently under debate. Here, we investigate directly the impact of the side chains by studying the bulky-substituted poly(3-(2,5-dioctylphenyl)thiophene) (PDOPT) and the common poly(3-hexylthiophene) (P3HT), both with a defined molecular weight and high regioregularity, using low-temperature single-chain photoluminescence (PL) spectroscopy and quantum-classical simulations. Surprisingly, the optical transition energy of PDOPT is significantly (∼2,000 cm−1 or 0.25 eV) red-shifted relative to P3HT despite a higher static and dynamic disorder in the former. We ascribe this red shift to a side-chain induced backbone planarization in PDOPT, supported by temperature-dependent ensemble PL spectroscopy. Our atomistic simulations reveal that the bulkier 2,5-dioctylphenyl side chains of PDOPT adopt a clear secondary helical structural motif and thus protect conjugation, i.e., enforce backbone planarity, whereas, for P3HT, this is not the case. These different degrees of planarity in both thiophenes do not result in different conjugation lengths, which we found to be similar. It is rather the stronger electronic coupling between the repeating units in the more planar PDOPT which gives rise to the observed spectral red shift as well as to a reduced calculated electron−hole polarization.


Langmuir ◽  
1998 ◽  
Vol 14 (19) ◽  
pp. 5425-5429 ◽  
Author(s):  
Mathias Brust ◽  
Donald Bethell ◽  
Christopher J. Kiely ◽  
David J. Schiffrin

2020 ◽  
Vol 109 ◽  
pp. 110257 ◽  
Author(s):  
Ammar Qasem ◽  
M.Y. Hassaan ◽  
M.G. Moustafa ◽  
Mohamed A.S. Hammam ◽  
H.Y. Zahran ◽  
...  

2019 ◽  
Vol 21 (32) ◽  
pp. 17729-17739 ◽  
Author(s):  
Alex Pifer Coleone ◽  
Leonardo Gois Lascane ◽  
Augusto Batagin-Neto

DFT calculations were used to evaluate the effect of side groups on the structural, optical and electronic properties of 3-substituted PPy derivatives. Simple relationships between the optoelectronic properties and Hammet parameters are proposed.


2015 ◽  
Vol 3 (38) ◽  
pp. 9842-9848 ◽  
Author(s):  
Kui Zhao ◽  
Xinhong Yu ◽  
Ruipeng Li ◽  
Aram Amassian ◽  
Yanchun Han

The mechanistic understanding of the intrinsic molecular self-assembly of conjugated polymers is of immense importance to control the microstructure development in organic semiconducting thin films, with a meaningful impact on charge transport and optoelectronic properties.


2012 ◽  
Vol 47 (9) ◽  
pp. 2487-2491 ◽  
Author(s):  
Younghun Hwang ◽  
Hyungmin Kim ◽  
Youngho Um ◽  
Hyoyeol Park

2009 ◽  
Vol 94 (14) ◽  
pp. 141907 ◽  
Author(s):  
R. Moubah ◽  
S. Colis ◽  
G. Schmerber ◽  
J. Petersen ◽  
A. Dinia

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