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Supramolecular Control of Organic Semiconductors Via Complementary Hydrogen Bonding.

Record Type:	Language materials, manuscript : Monograph/item
Title/Author:	Supramolecular Control of Organic Semiconductors Via Complementary Hydrogen Bonding./
Author:	Yee, Nathan.
Description:	1 online resource (178 pages)
Notes:	Source: Dissertations Abstracts International, Volume: 85-01, Section: B.
Contained By:	Dissertations Abstracts International85-01B.
Subject:	Crystal structure. -
Online resource:	click for full text (PQDT)
ISBN:	9798379863913

Supramolecular Control of Organic Semiconductors Via Complementary Hydrogen Bonding.
Yee, Nathan.

Supramolecular Control of Organic Semiconductors Via Complementary Hydrogen Bonding. - 1 online resource (178 pages)

Source: Dissertations Abstracts International, Volume: 85-01, Section: B.

Thesis (Ph.D.)--McGill University (Canada), 2023.

Includes bibliographical references

The band gap and the supramolecular structure of organic semiconductors (OSCs) are two key factors influencing their performance in optoelectronic devices. Complementary hydrogenbonding is a powerful interaction for controlling the supramolecular structure of OSCs. Recently, our lab showed that such hydrogen-bonding between donor and acceptor OSCs (bicomponent OSCs) also affects the band gaps of the donor and acceptor through a polarization effect, however the effect was weak. We thus sought a way to dramatically enhance this effect and exploit it as a tool in the design of bicomponent OSCs.In this thesis, we study charge-transfer complexes assembled via unidirectional two-point complementary bonding (DD...AA) of diindolopyrrole donors with various π-acceptors. We show how the very strong polarization effects of such hydrogen-bonding transforms weak donor and acceptors into very strong donor acceptor pairs. π-Stacking of the H-bonded pairs results in strong charge-transfer (HOMO-LUMO) interactions in their ground state, manifested in low energy optical absorption. By combining this effect with structural modifications of the donors and acceptors, we also demonstrate how such polarization effect can be exploited to control the band gaps of the complexes through a wide range (0.8 to 1.7 eV). The synthesis of the H-bonded complexes and their characterization using DFT analysis, optical and photoelectron spectroscopy, and X-ray crystallography, are described. Device studies in thin-film field-effect transistors were performed on selected H-bonded complexes to test their electrical properties and revealed ambipolar transport.We dive deeper into the effects of DD...AA H-bonding by comparing two structurally similar donor-acceptor complexes with and without hydrogen bonding. We show via X-ray crystallography, spectroscopic analysis and DFT, that the H-bonding enhances the donor-acceptor interactions, as manifested by the narrower band gap and shorter π-π distances of the H-bonded complex. Thin film transistors with the H-bonded complex fabricated by vacuum co-sublimation showed ambipolar charge transport, whereas no transistor behavior was observed for the complex without H-bonding.We also describe the serendipitous formation of a semiconducting indigoid by the degradation of the diindolopyrrole donor. The indigoid possessed intense long wavelength absorptions near 600 nm. Thin film OFETs based on the indigoid exhibited a higher hole mobility than its diindolopyrrole precursor. We also report a borylated derivative which is weakly emissive in the NIR.

Electronic reproduction.
Ann Arbor, Mich. :
ProQuest,
2024

Mode of access: World Wide Web

ISBN: 9798379863913Subjects--Topical Terms:

1372699
Crystal structure.
Index Terms--Genre/Form:

554714
Electronic books.

Supramolecular Control of Organic Semiconductors Via Complementary Hydrogen Bonding.
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500 $a Source: Dissertations Abstracts International, Volume: 85-01, Section: B.
500 $a Advisor: Perepichka, Dmytro.
502 $a Thesis (Ph.D.)--McGill University (Canada), 2023.
504 $a Includes bibliographical references
520 $a The band gap and the supramolecular structure of organic semiconductors (OSCs) are two key factors influencing their performance in optoelectronic devices. Complementary hydrogenbonding is a powerful interaction for controlling the supramolecular structure of OSCs. Recently, our lab showed that such hydrogen-bonding between donor and acceptor OSCs (bicomponent OSCs) also affects the band gaps of the donor and acceptor through a polarization effect, however the effect was weak. We thus sought a way to dramatically enhance this effect and exploit it as a tool in the design of bicomponent OSCs.In this thesis, we study charge-transfer complexes assembled via unidirectional two-point complementary bonding (DD...AA) of diindolopyrrole donors with various π-acceptors. We show how the very strong polarization effects of such hydrogen-bonding transforms weak donor and acceptors into very strong donor acceptor pairs. π-Stacking of the H-bonded pairs results in strong charge-transfer (HOMO-LUMO) interactions in their ground state, manifested in low energy optical absorption. By combining this effect with structural modifications of the donors and acceptors, we also demonstrate how such polarization effect can be exploited to control the band gaps of the complexes through a wide range (0.8 to 1.7 eV). The synthesis of the H-bonded complexes and their characterization using DFT analysis, optical and photoelectron spectroscopy, and X-ray crystallography, are described. Device studies in thin-film field-effect transistors were performed on selected H-bonded complexes to test their electrical properties and revealed ambipolar transport.We dive deeper into the effects of DD...AA H-bonding by comparing two structurally similar donor-acceptor complexes with and without hydrogen bonding. We show via X-ray crystallography, spectroscopic analysis and DFT, that the H-bonding enhances the donor-acceptor interactions, as manifested by the narrower band gap and shorter π-π distances of the H-bonded complex. Thin film transistors with the H-bonded complex fabricated by vacuum co-sublimation showed ambipolar charge transport, whereas no transistor behavior was observed for the complex without H-bonding.We also describe the serendipitous formation of a semiconducting indigoid by the degradation of the diindolopyrrole donor. The indigoid possessed intense long wavelength absorptions near 600 nm. Thin film OFETs based on the indigoid exhibited a higher hole mobility than its diindolopyrrole precursor. We also report a borylated derivative which is weakly emissive in the NIR.
520 $a La bande interdite et la structure supramoleculaire des semi-conducteurs organiques (OSC) sont deux facteurs cles qui influencent leurs performances dans les dispositifs optoelectroniques. La liaison hydrogene complementaire est une interaction puissante pour controler la structure supramoleculaire des OSCs. Recemment, notre laboratoire a montre que cette liaison hydrogene entre les OSC donneur et accepteur (OSC bicomposant) affecte egalement les bandes interdites du donneur et de l'accepteur par un effet de polarisation, mais cet effet etait faible. Nous avons donc cherche un moyen d'augmenter considerablement cet effet et de l'exploiter comme un outil dans la conception des OSCs bicomposants.Dans cette these, nous etudions les complexes de transfert de charge assembles via une liaison complementaire unidirectionnelle a deux points (DD...AA) de donneurs de diindolopyrrole avec divers π-accepteurs. Nous montrons comment les effets de polarisation tres forts de ces liaisons hydrogene transforment des donneurs et des accepteurs faibles en paires donneur-accepteur tres fortes. L'empilement π des paires liees par H entraine de fortes interactions de transfert de charge (HOMO-LUMO) dans leur etat fondamental, qui se manifestent par une absorption optique de faible energie. En combinant cet effet avec des modifications structurelles des donneurs et des accepteurs, nous demontrons egalement comment cet effet de polarisation peut etre exploite pour controler les bandes interdites des complexes dans une large gamme (0,8 a 1,7 eV). La synthese des complexes lies a l'hydrogene et leur caracterisation par analyse DFT, spectroscopie optique et photoelectronique, et cristallographie aux rayons X, sont decrites. Des etudes de dispositifs dans des transistors a effet de champ en couche mince ont ete realisees sur des complexes lies a l'hydrogene selectionnes afin de tester leurs proprietes electriques et ont revele un transport ambipolaire.Nous approfondissons les effets de la liaison H DD...AA en comparant deux complexes donneuraccepteur structurellement similaires avec et sans liaison hydrogene. Nous avons montre, par cristallographie aux rayons X, analyse spectroscopique et DFT, que la liaison H renforce les interactions donneur-accepteur, comme en temoignent la bande interdite plus etroite et les distances π-π plus courtes du complexe lie a l'hydrogene. Les transistors a couche mince avec le complexe lie a l'hydrogene, fabriques par co-sublimation sous vide, ont montre un transport de charge ambipolaire, alors qu'aucun comportement de transistor n'a ete observe pour le complexe sans liaison a l'hydrogene.Nous decrivons egalement la formation fortuite d'un indigoide semi-conducteur par la degradation du donneur de diindolopyrrole. L'indigoide possede des absorptions intenses de grandes longueurs d'onde pres de 600 nm. Les OFETs en film mince bases sur l'indigoide ont montre une mobilite des trous plus elevee que son precurseur DIP. Nous rapportons egalement un derive boryle qui est faiblement emissif dans le NIR.
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538 $a Mode of access: World Wide Web
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