Low and High Molecular Mass Dithienopyrrole–Naphthalene Bisimide Donor–Acceptor Compounds: Synthesis, Electrochemical and Spectroelectrochemical Behaviour

Renata Rybakiewicz; Eric D. Glowacki; Lukasz Skorka; Sandra Pluczyk; Pawel Zassowski; Dogukan Hazar Apaydin; Mieczyslaw Lapkowski; Malgorzata Zagorska; Adam Pron

doi:10.1002/chem.201604672

Low and High Molecular Mass Dithienopyrrole–Naphthalene Bisimide Donor–Acceptor Compounds: Synthesis, Electrochemical and Spectroelectrochemical Behaviour

Renata Rybakiewicz
, Eric D. Glowacki
, Lukasz Skorka
, Sandra Pluczyk
, Pawel Zassowski
, Dogukan Hazar Apaydin
, Mieczyslaw Lapkowski
, Malgorzata Zagorska
, Adam Pron

Department of Physical Chemistry and Technology of Polymers (RCH/RCH4)

Cardinal Stefan Wyszynski University
Warsaw University of Technology
Linköping University
Silesian University of Technology
Johannes Kepler University Linz
Polish Academy of Sciences

Research output: Contribution to journal › Article › peer-review

20 Citations (Scopus)

Abstract

Two low molecular weight electroactive donor–acceptor–donor (DAD)-type molecules are reported, namely naphthalene bisimide (NBI) symmetrically core-functionalized with dithienopyrrole (NBI-(DTP)₂) and an asymmetric core-functionalized naphthalene bisimide with dithienopyrrole (DTP) substituent on one side and 2-ethylhexylamine on the other side (NBI-DTP-NHEtHex). Both compounds are characterized by low optical bandgaps (1.52 and 1.65 eV, respectively). NBI-(DTP)₂undergoes oxidative electropolymerization giving the electroactive polymer of ambipolar character. Its two-step reversible reduction and oxidation is corroborated by complementary EPR and UV/Vis–NIR spectroelectrochemical investigations. The polymer turned out to be electrochemically active not only in aprotic solvents but also in aqueous electrolytes, showing a distinct photocathodic current attributed to proton reduction. Additionally, poly(NBI-(DTP)₂) was successfully tested as a photodiode material.

Original language	English
Pages (from-to)	2839-2851
Number of pages	13
Journal	Chemistry - A European Journal
Volume	23
Issue number	12
DOIs	https://doi.org/10.1002/chem.201604672
Publication status	Published - 24 Feb 2017

Keywords

dithienopyrrole
electrochemistry
naphthalene bisimide
photodiode
polymerization

ASJC Scopus subject areas

Catalysis
General Chemistry
Organic Chemistry

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10.1002/chem.201604672

Cite this

Rybakiewicz, R., Glowacki, E. D., Skorka, L., Pluczyk, S., Zassowski, P., Apaydin, D. H., Lapkowski, M., Zagorska, M., & Pron, A. (2017). Low and High Molecular Mass Dithienopyrrole–Naphthalene Bisimide Donor–Acceptor Compounds: Synthesis, Electrochemical and Spectroelectrochemical Behaviour. Chemistry - A European Journal, 23(12), 2839-2851. https://doi.org/10.1002/chem.201604672

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title = "Low and High Molecular Mass Dithienopyrrole{\textendash}Naphthalene Bisimide Donor{\textendash}Acceptor Compounds: Synthesis, Electrochemical and Spectroelectrochemical Behaviour",

abstract = "Two low molecular weight electroactive donor{\textendash}acceptor{\textendash}donor (DAD)-type molecules are reported, namely naphthalene bisimide (NBI) symmetrically core-functionalized with dithienopyrrole (NBI-(DTP)2) and an asymmetric core-functionalized naphthalene bisimide with dithienopyrrole (DTP) substituent on one side and 2-ethylhexylamine on the other side (NBI-DTP-NHEtHex). Both compounds are characterized by low optical bandgaps (1.52 and 1.65 eV, respectively). NBI-(DTP)2undergoes oxidative electropolymerization giving the electroactive polymer of ambipolar character. Its two-step reversible reduction and oxidation is corroborated by complementary EPR and UV/Vis{\textendash}NIR spectroelectrochemical investigations. The polymer turned out to be electrochemically active not only in aprotic solvents but also in aqueous electrolytes, showing a distinct photocathodic current attributed to proton reduction. Additionally, poly(NBI-(DTP)2) was successfully tested as a photodiode material.",

keywords = "dithienopyrrole, electrochemistry, naphthalene bisimide, photodiode, polymerization",

author = "Renata Rybakiewicz and Glowacki, \{Eric D.\} and Lukasz Skorka and Sandra Pluczyk and Pawel Zassowski and Apaydin, \{Dogukan Hazar\} and Mieczyslaw Lapkowski and Malgorzata Zagorska and Adam Pron",

note = "Publisher Copyright: {\textcopyright} 2017 Wiley-VCH Verlag GmbH \& Co. KGaA, Weinheim",

year = "2017",

month = feb,

day = "24",

doi = "10.1002/chem.201604672",

language = "English",

volume = "23",

pages = "2839--2851",

journal = "Chemistry - A European Journal",

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Rybakiewicz, R, Glowacki, ED, Skorka, L, Pluczyk, S, Zassowski, P, Apaydin, DH, Lapkowski, M, Zagorska, M & Pron, A 2017, 'Low and High Molecular Mass Dithienopyrrole–Naphthalene Bisimide Donor–Acceptor Compounds: Synthesis, Electrochemical and Spectroelectrochemical Behaviour', Chemistry - A European Journal, vol. 23, no. 12, pp. 2839-2851. https://doi.org/10.1002/chem.201604672

Low and High Molecular Mass Dithienopyrrole–Naphthalene Bisimide Donor–Acceptor Compounds: Synthesis, Electrochemical and Spectroelectrochemical Behaviour. / Rybakiewicz, Renata; Glowacki, Eric D.; Skorka, Lukasz et al.
In: Chemistry - A European Journal, Vol. 23, No. 12, 24.02.2017, p. 2839-2851.

Research output: Contribution to journal › Article › peer-review

TY - JOUR

T1 - Low and High Molecular Mass Dithienopyrrole–Naphthalene Bisimide Donor–Acceptor Compounds

T2 - Synthesis, Electrochemical and Spectroelectrochemical Behaviour

AU - Rybakiewicz, Renata

AU - Glowacki, Eric D.

AU - Skorka, Lukasz

AU - Pluczyk, Sandra

AU - Zassowski, Pawel

AU - Apaydin, Dogukan Hazar

AU - Lapkowski, Mieczyslaw

AU - Zagorska, Malgorzata

AU - Pron, Adam

PY - 2017/2/24

Y1 - 2017/2/24

N2 - Two low molecular weight electroactive donor–acceptor–donor (DAD)-type molecules are reported, namely naphthalene bisimide (NBI) symmetrically core-functionalized with dithienopyrrole (NBI-(DTP)2) and an asymmetric core-functionalized naphthalene bisimide with dithienopyrrole (DTP) substituent on one side and 2-ethylhexylamine on the other side (NBI-DTP-NHEtHex). Both compounds are characterized by low optical bandgaps (1.52 and 1.65 eV, respectively). NBI-(DTP)2undergoes oxidative electropolymerization giving the electroactive polymer of ambipolar character. Its two-step reversible reduction and oxidation is corroborated by complementary EPR and UV/Vis–NIR spectroelectrochemical investigations. The polymer turned out to be electrochemically active not only in aprotic solvents but also in aqueous electrolytes, showing a distinct photocathodic current attributed to proton reduction. Additionally, poly(NBI-(DTP)2) was successfully tested as a photodiode material.

AB - Two low molecular weight electroactive donor–acceptor–donor (DAD)-type molecules are reported, namely naphthalene bisimide (NBI) symmetrically core-functionalized with dithienopyrrole (NBI-(DTP)2) and an asymmetric core-functionalized naphthalene bisimide with dithienopyrrole (DTP) substituent on one side and 2-ethylhexylamine on the other side (NBI-DTP-NHEtHex). Both compounds are characterized by low optical bandgaps (1.52 and 1.65 eV, respectively). NBI-(DTP)2undergoes oxidative electropolymerization giving the electroactive polymer of ambipolar character. Its two-step reversible reduction and oxidation is corroborated by complementary EPR and UV/Vis–NIR spectroelectrochemical investigations. The polymer turned out to be electrochemically active not only in aprotic solvents but also in aqueous electrolytes, showing a distinct photocathodic current attributed to proton reduction. Additionally, poly(NBI-(DTP)2) was successfully tested as a photodiode material.

KW - dithienopyrrole

KW - electrochemistry

KW - naphthalene bisimide

KW - photodiode

KW - polymerization

UR - https://www.scopus.com/pages/publications/85011392080

U2 - 10.1002/chem.201604672

DO - 10.1002/chem.201604672

M3 - Article

C2 - 28059477

AN - SCOPUS:85011392080

SN - 0947-6539

VL - 23

SP - 2839

EP - 2851

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

IS - 12

ER -

Low and High Molecular Mass Dithienopyrrole–Naphthalene Bisimide Donor–Acceptor Compounds: Synthesis, Electrochemical and Spectroelectrochemical Behaviour

Abstract

Keywords

ASJC Scopus subject areas

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