Highly Electron‐Donating Bipyranylidene Derivatives: Potential n‐Type Dopants for Organic Thermoelectrics

The design, synthesis, and characterization of new electron‐donor molecules with the closed‐shell electronic structure are described. The molecular design features the use of a bipyranylidene 7π‐electron system together with strong electron‐donating substituents, namely, methoxy and dimethylamino gr...

Descripción completa

Guardado en:

Detalles Bibliográficos
Autores principales:	Takaya Matsuo, Kohsuke Kawabata, Kazuo Takimiya
Formato:	article
Lenguaje:	EN
Publicado:	Wiley-VCH 2021
Materias:	molecular designs n-type dopants n-type organic thermoelectrics Environmental technology. Sanitary engineering TD1-1066 Renewable energy sources TJ807-830
Acceso en línea:	https://doaj.org/article/73afce0216b445fa8367057def5eae97
Etiquetas:	Agregar Etiqueta Sin Etiquetas, Sea el primero en etiquetar este registro!

id	oai:doaj.org-article:73afce0216b445fa8367057def5eae97
record_format	dspace
spelling	oai:doaj.org-article:73afce0216b445fa8367057def5eae972021-11-04T09:03:08ZHighly Electron‐Donating Bipyranylidene Derivatives: Potential n‐Type Dopants for Organic Thermoelectrics2699-941210.1002/aesr.202100084https://doaj.org/article/73afce0216b445fa8367057def5eae972021-11-01T00:00:00Zhttps://doi.org/10.1002/aesr.202100084https://doaj.org/toc/2699-9412The design, synthesis, and characterization of new electron‐donor molecules with the closed‐shell electronic structure are described. The molecular design features the use of a bipyranylidene 7π‐electron system together with strong electron‐donating substituents, namely, methoxy and dimethylamino groups, which realizes the highest occupied molecular orbitals (HOMOs) as high as or higher than 4.0 eV below the vacuum level. Such high‐lying energy levels of the HOMOs make them potential n‐type dopants for organic thermoelectrics, and it turned out that they are capable of electron‐doping to representative n‐type semiconducting polymers, poly([N,N′‐bis(2‐octyldodecyl)‐naphthalene‐1,4,5,8‐bis(dicarboximide)‐2,6‐diyl]‐alt‐5,5′‐(2,2′‐bithiophene)) (N2200) and poly(benzimidazobenzophenanthroline) (BBL). The resulting doped polymers show decent thermoelectric characteristics with the power factors of 5.7 × 10−3 (N2200) and 1.62 μW m−1 K−2 (BBL), respectively. These values are almost comparable with those of the polymers doped with 4‐(2,3‐dihydro‐1,3‐dimethyl‐1H‐benzimidazol‐2‐yl)‐N,N‐dimethylbenzenamine (N‐DMBI), a representative n‐type dopant frequently used in the development of n‐type polymer thermoelectrics. These results indicate that even with the molecules possessing the closed‐shell electronic structure, efficient n‐type dopants can be realized, implying that versatile molecular fragments with electron‐donating natures could be used to develop novel superior n‐type dopants for organic thermoelectric applications.Takaya MatsuoKohsuke KawabataKazuo TakimiyaWiley-VCHarticlemolecular designsn-type dopantsn-type organic thermoelectricsEnvironmental technology. Sanitary engineeringTD1-1066Renewable energy sourcesTJ807-830ENAdvanced Energy & Sustainability Research, Vol 2, Iss 11, Pp n/a-n/a (2021)
institution	DOAJ
collection	DOAJ
language	EN
topic	molecular designs n-type dopants n-type organic thermoelectrics Environmental technology. Sanitary engineering TD1-1066 Renewable energy sources TJ807-830
spellingShingle	molecular designs n-type dopants n-type organic thermoelectrics Environmental technology. Sanitary engineering TD1-1066 Renewable energy sources TJ807-830 Takaya Matsuo Kohsuke Kawabata Kazuo Takimiya Highly Electron‐Donating Bipyranylidene Derivatives: Potential n‐Type Dopants for Organic Thermoelectrics
description	The design, synthesis, and characterization of new electron‐donor molecules with the closed‐shell electronic structure are described. The molecular design features the use of a bipyranylidene 7π‐electron system together with strong electron‐donating substituents, namely, methoxy and dimethylamino groups, which realizes the highest occupied molecular orbitals (HOMOs) as high as or higher than 4.0 eV below the vacuum level. Such high‐lying energy levels of the HOMOs make them potential n‐type dopants for organic thermoelectrics, and it turned out that they are capable of electron‐doping to representative n‐type semiconducting polymers, poly([N,N′‐bis(2‐octyldodecyl)‐naphthalene‐1,4,5,8‐bis(dicarboximide)‐2,6‐diyl]‐alt‐5,5′‐(2,2′‐bithiophene)) (N2200) and poly(benzimidazobenzophenanthroline) (BBL). The resulting doped polymers show decent thermoelectric characteristics with the power factors of 5.7 × 10−3 (N2200) and 1.62 μW m−1 K−2 (BBL), respectively. These values are almost comparable with those of the polymers doped with 4‐(2,3‐dihydro‐1,3‐dimethyl‐1H‐benzimidazol‐2‐yl)‐N,N‐dimethylbenzenamine (N‐DMBI), a representative n‐type dopant frequently used in the development of n‐type polymer thermoelectrics. These results indicate that even with the molecules possessing the closed‐shell electronic structure, efficient n‐type dopants can be realized, implying that versatile molecular fragments with electron‐donating natures could be used to develop novel superior n‐type dopants for organic thermoelectric applications.
format	article
author	Takaya Matsuo Kohsuke Kawabata Kazuo Takimiya
author_facet	Takaya Matsuo Kohsuke Kawabata Kazuo Takimiya
author_sort	Takaya Matsuo
title	Highly Electron‐Donating Bipyranylidene Derivatives: Potential n‐Type Dopants for Organic Thermoelectrics
title_short	Highly Electron‐Donating Bipyranylidene Derivatives: Potential n‐Type Dopants for Organic Thermoelectrics
title_full	Highly Electron‐Donating Bipyranylidene Derivatives: Potential n‐Type Dopants for Organic Thermoelectrics
title_fullStr	Highly Electron‐Donating Bipyranylidene Derivatives: Potential n‐Type Dopants for Organic Thermoelectrics
title_full_unstemmed	Highly Electron‐Donating Bipyranylidene Derivatives: Potential n‐Type Dopants for Organic Thermoelectrics
title_sort	highly electron‐donating bipyranylidene derivatives: potential n‐type dopants for organic thermoelectrics
publisher	Wiley-VCH
publishDate	2021
url	https://doaj.org/article/73afce0216b445fa8367057def5eae97
work_keys_str_mv	AT takayamatsuo highlyelectrondonatingbipyranylidenederivativespotentialntypedopantsfororganicthermoelectrics AT kohsukekawabata highlyelectrondonatingbipyranylidenederivativespotentialntypedopantsfororganicthermoelectrics AT kazuotakimiya highlyelectrondonatingbipyranylidenederivativespotentialntypedopantsfororganicthermoelectrics
_version_	1718444969120759808

Highly Electron‐Donating Bipyranylidene Derivatives: Potential n‐Type Dopants for Organic Thermoelectrics

Ejemplares similares