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  1. Article ; Online: Dibenzo[a,e]pentalenes with Low-Lying LUMO Energy Levels as Potential n-Type Materials.

    Grenz, David C / Schmidt, Maximilian / Kratzert, Daniel / Esser, Birgit

    The Journal of organic chemistry

    2018  Volume 83, Issue 2, Page(s) 656–663

    Abstract: Ambipolar organic semiconductors are of high interest for organic field-effect transistors. For n-type conduction, low LUMO energies are required. Dibenzo[a,e]pentalenes (DBPs) are promising compounds; however, few derivatives exist with energetically ... ...

    Abstract Ambipolar organic semiconductors are of high interest for organic field-effect transistors. For n-type conduction, low LUMO energies are required. Dibenzo[a,e]pentalenes (DBPs) are promising compounds; however, few derivatives exist with energetically low-lying LUMO levels. Here, we present DBP derivatives with LUMO energies down to -3.73 eV and small bandgaps down to 1.63 eV determined through cyclic voltammetry, UV/vis absorption spectroscopy, and TDDFT calculations. Single-crystal X-ray diffraction analysis revealed a 1D π-stacking mode. The addition of arylalkynyl substituents at the five-membered rings in a facile and versatile synthetic route allowed for tuning of the band gaps and LUMO energies. The synthetic route can easily be modified to access a variety of DBP derivatives. The LUMO energies of the DBP derivatives presented herein make them attractive for an application in n-type or ambipolar field-effect transistors.
    Language English
    Publishing date 2018--19
    Publishing country United States
    Document type Journal Article ; Research Support, Non-U.S. Gov't
    ZDB-ID 123490-0
    ISSN 1520-6904 ; 0022-3263
    ISSN (online) 1520-6904
    ISSN 0022-3263
    DOI 10.1021/acs.joc.7b02250
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  2. Article ; Online: Spiroconjugated Tetraaminospirenes as Donors in Color-Tunable Charge-Transfer Emitters with Donor-Acceptor Structure.

    Grenz, David C / Rose, Daniel / Wössner, Jan S / Wilbuer, Jennifer / Adler, Florin / Hermann, Mathias / Chan, Chin-Yiu / Adachi, Chihaya / Esser, Birgit

    Chemistry (Weinheim an der Bergstrasse, Germany)

    2021  Volume 28, Issue 6, Page(s) e202104150

    Abstract: Charge-transfer emitters are attractive due to their color tunability and potentially high photoluminescence quantum yields (PLQYs). We herein present tetraaminospirenes as donor moieties, which, in combination with a variety of acceptors, furnished 12 ... ...

    Abstract Charge-transfer emitters are attractive due to their color tunability and potentially high photoluminescence quantum yields (PLQYs). We herein present tetraaminospirenes as donor moieties, which, in combination with a variety of acceptors, furnished 12 charge-transfer emitters with a range of emission colors and PLQYs of up to 99 %. The spatial separation of their frontier molecular orbitals was obtained through careful structural design, and two DA structures were confirmed by X-ray crystallography. A range of photophysical measurements supported by DFT calculations shed light on the optoelectronic properties of this new family of spiro-NN-donor-acceptor dyes.
    Language English
    Publishing date 2021-12-16
    Publishing country Germany
    Document type Journal Article
    ZDB-ID 1478547-X
    ISSN 1521-3765 ; 0947-6539
    ISSN (online) 1521-3765
    ISSN 0947-6539
    DOI 10.1002/chem.202104150
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  3. Article: Dibenzo[a,e]pentalenes with Low-Lying LUMO Energy Levels as Potential n-Type Materials

    Grenz, David C / Birgit Esser / Daniel Kratzert / Maximilian Schmidt

    Journal of organic chemistry. 2018 Jan. 19, v. 83, no. 2

    2018  

    Abstract: Ambipolar organic semiconductors are of high interest for organic field-effect transistors. For n-type conduction, low LUMO energies are required. Dibenzo[a,e]pentalenes (DBPs) are promising compounds; however, few derivatives exist with energetically ... ...

    Abstract Ambipolar organic semiconductors are of high interest for organic field-effect transistors. For n-type conduction, low LUMO energies are required. Dibenzo[a,e]pentalenes (DBPs) are promising compounds; however, few derivatives exist with energetically low-lying LUMO levels. Here, we present DBP derivatives with LUMO energies down to −3.73 eV and small bandgaps down to 1.63 eV determined through cyclic voltammetry, UV/vis absorption spectroscopy, and TDDFT calculations. Single-crystal X-ray diffraction analysis revealed a 1D π-stacking mode. The addition of arylalkynyl substituents at the five-membered rings in a facile and versatile synthetic route allowed for tuning of the band gaps and LUMO energies. The synthetic route can easily be modified to access a variety of DBP derivatives. The LUMO energies of the DBP derivatives presented herein make them attractive for an application in n-type or ambipolar field-effect transistors.
    Keywords chemical reactions ; chemical structure ; energy ; organic chemistry ; organic compounds ; spectroscopy ; transistors ; X-ray diffraction
    Language English
    Dates of publication 2018-0119
    Size p. 656-663.
    Publishing place American Chemical Society
    Document type Article
    ZDB-ID 123490-0
    ISSN 1520-6904 ; 0022-3263
    ISSN (online) 1520-6904
    ISSN 0022-3263
    DOI 10.1021/acs.joc.7b02250
    Database NAL-Catalogue (AGRICOLA)

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    In stock of ZB MED Bonn / Germany

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  4. Article: Peripherally Donor-Installed 7,8-Diaza[5]helicenes as a Platform for Helical Luminophores

    Ikari, Yuta / Kaihara, Takahito / Goto, Shimpei / Bovenkerk, Marcel / Grenz, David C. / Esser, Birgit / Ferreira, Marli / Stachelek, Patrycja / Data, Przemyslaw / Yoshida, Takumu / Ikai, Tomoyuki / Tohnai, Norimitsu / Minakata, Satoshi / Takeda, Youhei

    Synthesis

    2020  Volume 53, Issue 09, Page(s) 1584–1596

    Abstract: A new family of emissive donor–acceptor–donor (D-A-D) compounds has been developed by introducing two electron donors into the 7,8-diaza[5]helicene core as a novel helical electron acceptor. The X-ray crystallographic analyses revealed the uniquely ... ...

    Abstract A new family of emissive donor–acceptor–donor (D-A-D) compounds has been developed by introducing two electron donors into the 7,8-diaza[5]helicene core as a novel helical electron acceptor. The X-ray crystallographic analyses revealed the uniquely twisted and helical structures of these compounds in the solid states. Notably, some D-A-D compounds developed herein display distinct mechanochromic luminescence (MCL) in the solid state, and a D-A-D helicene shows circularly polarized luminescence (CPL) with a relatively high luminescence dissymmetry factor g lum of ca. 10 –3. Time-resolved spectroscopic analysis revealed the aspects of thermally activated delayed fluorescence characters of the helicenes. Furthermore, the emissive helicenes were applied to organic light-emitting diodes as emitters.
    Keywords helical structures ; mechanochromism ; circularly polarized luminescence ; donor-acceptor ; charge-transfer ; organic light-emitting diodes ; amination
    Language English
    Publishing date 2020-12-28
    Publisher Georg Thieme Verlag KG
    Publishing place Stuttgart ; New York
    Document type Article
    ZDB-ID 2033062-5
    ISSN 1437-210X ; 0039-7881
    ISSN (online) 1437-210X
    ISSN 0039-7881
    DOI 10.1055/a-1343-5810
    Database Thieme publisher's database

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