Borylated Arylamine-Benzothiadiazole Donor-Acceptor Materials as Low LUMO, Low Band-Gap Chromophores

Daniel Crossley; Rosanne  Goh; Jessica Cid; Inigo Vitorica-Yrezabal; Michael Turner; Michael Ingleson

doi:10.1021/acs.organomet.7b00188

Borylated Arylamine-Benzothiadiazole Donor-Acceptor Materials as Low LUMO, Low Band-Gap Chromophores

Daniel Crossley, Rosanne Goh, Jessica Cid, Inigo Vitorica-Yrezabal, Michael Turner, Michael Ingleson

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Abstract

Fused and ladder type benzothiadiazole-arylamine donor-acceptor C,N-chelated boron complexes were synthesized through direct electrophilic C-H borylation. The frontier molecular orbital energy levels of the borylated materials then could be modulated through variation of the exocyclic boron substituents by transmetallation with different diarylzinc reagents. The borylated materials possessed low band-gaps and low LUMO energy levels with a number of examples also showing significant absorbance > 700 nm; however, low photoluminescence quantum yields were found for all these borylated compounds.

Original language	English
Journal	Organometallics
Volume	36
Issue number	14
Early online date	25 Apr 2017
DOIs	https://doi.org/10.1021/acs.organomet.7b00188
Publication status	Published - 2017

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10.1021/acs.organomet.7b00188

TPA_CBzBT OM-RevisedAccepted author manuscript, 1.03 MB

CCDC 1528512: Experimental Crystal Structure Determination
Crossley, D. (Contributor), Goh, R. (Contributor), Cid, J. (Contributor), Vitorica-Yrezabal, I. (Contributor), Turner, M. (Contributor) & Ingleson, M. (Contributor), Cambridge Crystallographic Data Centre, 1 Jan 2017
DOI: 10.5517/ccdc.csd.cc1n9jvb, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc1n9jvb&sid=DataCite
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title = "Borylated Arylamine-Benzothiadiazole Donor-Acceptor Materials as Low LUMO, Low Band-Gap Chromophores",

abstract = "Fused and ladder type benzothiadiazole-arylamine donor-acceptor C,N-chelated boron complexes were synthesized through direct electrophilic C-H borylation. The frontier molecular orbital energy levels of the borylated materials then could be modulated through variation of the exocyclic boron substituents by transmetallation with different diarylzinc reagents. The borylated materials possessed low band-gaps and low LUMO energy levels with a number of examples also showing significant absorbance > 700 nm; however, low photoluminescence quantum yields were found for all these borylated compounds.",

author = "Daniel Crossley and Rosanne Goh and Jessica Cid and Inigo Vitorica-Yrezabal and Michael Turner and Michael Ingleson",

year = "2017",

doi = "10.1021/acs.organomet.7b00188",

language = "English",

volume = "36",

journal = "Organometallics",

issn = "0276-7333",

publisher = "American Chemical Society",

number = "14",

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TY - JOUR

T1 - Borylated Arylamine-Benzothiadiazole Donor-Acceptor Materials as Low LUMO, Low Band-Gap Chromophores

AU - Crossley, Daniel

AU - Goh, Rosanne

AU - Cid, Jessica

AU - Vitorica-Yrezabal, Inigo

AU - Turner, Michael

AU - Ingleson, Michael

PY - 2017

Y1 - 2017

N2 - Fused and ladder type benzothiadiazole-arylamine donor-acceptor C,N-chelated boron complexes were synthesized through direct electrophilic C-H borylation. The frontier molecular orbital energy levels of the borylated materials then could be modulated through variation of the exocyclic boron substituents by transmetallation with different diarylzinc reagents. The borylated materials possessed low band-gaps and low LUMO energy levels with a number of examples also showing significant absorbance > 700 nm; however, low photoluminescence quantum yields were found for all these borylated compounds.

AB - Fused and ladder type benzothiadiazole-arylamine donor-acceptor C,N-chelated boron complexes were synthesized through direct electrophilic C-H borylation. The frontier molecular orbital energy levels of the borylated materials then could be modulated through variation of the exocyclic boron substituents by transmetallation with different diarylzinc reagents. The borylated materials possessed low band-gaps and low LUMO energy levels with a number of examples also showing significant absorbance > 700 nm; however, low photoluminescence quantum yields were found for all these borylated compounds.

U2 - 10.1021/acs.organomet.7b00188

DO - 10.1021/acs.organomet.7b00188

M3 - Article

SN - 0276-7333

VL - 36

JO - Organometallics

JF - Organometallics

IS - 14

ER -

Borylated Arylamine-Benzothiadiazole Donor-Acceptor Materials as Low LUMO, Low Band-Gap Chromophores

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CCDC 1528512: Experimental Crystal Structure Determination

Cite this