Asian Journal of Organic Chemistry

Cover image for Vol. 3 Issue 2

Special Issue: Pi-Conjugated Compounds for Organic Electronics

February 2014

Volume 3, Issue 2

Pages 85–224

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Editorial
    4. Graphical Abstract
    5. News
    6. Focus Review
    7. Communications
    8. Full Papers
    1. You have free access to this content
      Cover Picture: Hydroxyphenyl-Substituted Benzophosphole Oxides: Impact of the Intramolecular Hydrogen Bond on the Fluorescence Properties (Asian J. Org. Chem. 2/2014) (page 85)

      Prof. Dr. Aiko Fukazawa, Hiroshi Osaki and Prof. Dr. Shigehiro Yamaguchi

      Version of Record online: 14 FEB 2014 | DOI: 10.1002/ajoc.201490002

      Thumbnail image of graphical abstract

      A molecule that has distinct fluorescence properties that are dependent on the environment of the sample has emerged as a basis of the environment-responsive luminescent materials. In their Communication on page 122 ff., Shigehiro Yamaguchi and co-workers designed and synthesized 2-(o-hydroxyphenyl)-substituted benzophosphole oxides, which can form an intramolecular hydrogen bond between the hydroxy group and the phosphine oxide moiety. A 3-phenylated derivative fluoresces in several specific solvents that have hydrogen-bond-accepting abilities, whereas it is virtually non-emissive in toluene, CH2Cl2, and MeCN. Switching of the hydrogen bonds can be a mechanism for controlling the fluorescence properties of phosphole-oxide-based π-electron systems.

  2. Editorial

    1. Top of page
    2. Cover Picture
    3. Editorial
    4. Graphical Abstract
    5. News
    6. Focus Review
    7. Communications
    8. Full Papers
    1. You have free access to this content
      Connected Chemistry (page 87)

      Prof. Dr. Deqing Zhang

      Version of Record online: 4 FEB 2014 | DOI: 10.1002/ajoc.201400007

  3. Graphical Abstract

    1. Top of page
    2. Cover Picture
    3. Editorial
    4. Graphical Abstract
    5. News
    6. Focus Review
    7. Communications
    8. Full Papers
  4. News

    1. Top of page
    2. Cover Picture
    3. Editorial
    4. Graphical Abstract
    5. News
    6. Focus Review
    7. Communications
    8. Full Papers
  5. Focus Review

    1. Top of page
    2. Cover Picture
    3. Editorial
    4. Graphical Abstract
    5. News
    6. Focus Review
    7. Communications
    8. Full Papers
    1. Phosphorescent Compounds

      Hosts for High-Performance Phosphorescent Organic Light-Emitting Diodes Based on Carbazole Derivatives (pages 102–112)

      Prof. Dr. Hongji Jiang

      Version of Record online: 4 FEB 2014 | DOI: 10.1002/ajoc.201300234

      Thumbnail image of graphical abstract

      Seeing the light: Up-to-date methods for chemical modifications to obtain hosts for high-performance, phosphorescent, organic light-emitting diodes based on carbazole derivatives are presented in detail. These methods include heterocycle replacement and extension of the conjugated structure of the carbazole skeleton.

  6. Communications

    1. Top of page
    2. Cover Picture
    3. Editorial
    4. Graphical Abstract
    5. News
    6. Focus Review
    7. Communications
    8. Full Papers
    1. Diazapentacene Diimides

      Synthesis and Properties of Diazapentacene Diimides (pages 114–117)

      Cheng Li, Dr. Wei Jiang, Prof. Dr. Xiaozhang Zhu and Prof. Dr. Zhaohui Wang

      Version of Record online: 13 NOV 2013 | DOI: 10.1002/ajoc.201300195

      Thumbnail image of graphical abstract

      Double-crossed: Diazapentacene diimides have been synthesized effectively based on the double cross-coupling of zirconacyclopentadienes with unilateral dibromonaphthalene diimides, and subsequent dehydrogenative aromatization. These diimides have interesting optoelectronic properties with deep LUMO levels and small band gaps.

    2. Mechanochromism

      An Aggregation-Induced Emission Luminogen with Efficient Luminescent Mechanochromism and Optical Waveguiding Properties (pages 118–121)

      Dr. Na Zhao, Chuang Zhang, Dr. Jacky W. Y. Lam, Prof. Yong Sheng Zhao and Prof. Ben Zhong Tang

      Version of Record online: 20 DEC 2013 | DOI: 10.1002/ajoc.201300223

      Thumbnail image of graphical abstract

      Guiding light: A yellow aggregation-induced emission luminogen (TPE-DCV) was synthesized by decorating a tetraphenylethene group with two dicyanovinyl units. This compound exhibits reversible luminescent mechanochromism. Two shapes of microcrystal of TPE-DCV display outstanding optical waveguiding behavior.

    3. Phospholes

      Hydroxyphenyl-Substituted Benzophosphole Oxides: Impact of the Intramolecular Hydrogen Bond on the Fluorescence Properties (pages 122–127)

      Prof. Dr. Aiko Fukazawa, Hiroshi Osaki and Prof. Dr. Shigehiro Yamaguchi

      Version of Record online: 27 DEC 2013 | DOI: 10.1002/ajoc.201300227

      Thumbnail image of graphical abstract

      In hyd-ing: Benzophosphole oxides with an o-hydroxyphenyl group at the 2-position have been synthesized. A 3-phenylated derivative is fluorescent in solvents that accept hydrogen bonds, but virtually non-emissive in toluene, CH2Cl2, and MeCN. This suggests an excited-state character switch from a non-emissive excited-state intramolecular proton transfer (ESIPT) state in weak hydrogen-bonding solvents to an emissive excited state in hydrogen-bonding solvents.

    4. Organogelators

      A Perylene Bisimide Organogelator for Chlorinated Solvents (pages 128–132)

      Dr. Xu Lin, Misaki Hirono, Hiroki Kurata, Dr. Tomohiro Seki, Yukihiro Maruya, Prof. Dr. Ken-ichi Nakayama and Prof. Dr. Shiki Yagai

      Version of Record online: 29 JAN 2014 | DOI: 10.1002/ajoc.201300252

      Thumbnail image of graphical abstract

      Gelling well: A perylene-bisimide-functionalized flexible bisurea was synthesized and its gelation ability in chlorinated solvents was investigated. The compound forms organogels in CHCl3 and Cl2CHCHCl2, whereas a viscous liquid was obtained in CCl4.

  7. Full Papers

    1. Top of page
    2. Cover Picture
    3. Editorial
    4. Graphical Abstract
    5. News
    6. Focus Review
    7. Communications
    8. Full Papers
    1. Organic Semiconductors

      Thiazolothiazole-Containing Ambipolar Organic Semiconductor with Balanced Hole and Electron Mobility (pages 134–139)

      Yuanyuan Wang, Dr. Qiuliu Huang, Prof. Zhiqiang Liu and Prof. Hongxiang Li

      Version of Record online: 21 NOV 2013 | DOI: 10.1002/ajoc.201300184

      Thumbnail image of graphical abstract

      Thiazolothiazole-containing organic semiconductors DH-TTFZTT and DPCO-TTFZTT were synthesized. Thin-film transistor characteristics showed that DH-TTFZTT behaves as a p-channel semiconductor with a hole mobility of approximately 2×10−2 cm2 V−1 s−1. DPCO-TTFZTT-based devices have balanced ambipolar performance. The hole and electron mobilities are 2.41×10−2 cm2 V−1 s−1 and 2.36×10−2 cm2 V−1 s−1 respectively.

    2. Dye-Sensitized Solar Cells

      Pyridine-N-Oxide 2-Carboxylic Acid: An Acceptor Group for Organic Sensitizers with Enhanced Anchoring Stability in Dye-Sensitized Solar Cells (pages 140–152)

      Bianca Cecconi, Dr. Alessandro Mordini, Dr. Gianna Reginato, Dr. Lorenzo Zani, Prof. Dr. Maurizio Taddei, Dr. Fabrizia Fabrizi de Biani, Dr. Filippo De Angelis, Gabriele Marotta, Dr. Paolo Salvatori and Dr. Massimo Calamante

      Version of Record online: 27 JAN 2014 | DOI: 10.1002/ajoc.201300267

      Thumbnail image of graphical abstract

      A sensitive soul: A D-π-A organic dye carrying a pyridine-N-oxide 2-carboxylic acid anchoring group was synthesized and used as a sensitizer for TiO2. Desorption kinetics experiments demonstrated that the new dye adsorbs onto TiO2 more strongly than a classic cyanoacrylic-acid-containing dye. When used as a sensitizer in a dye-sensitized solar cell, the power conversion efficiency of the sensitizer was approximately 66 % of that of a reference dye.

    3. Dye-Sensitized Solar Cells Based on Functionally Separated D-π-A Dyes with 2-Cyanopyridine as an Electron-Accepting and Anchoring Group (pages 153–160)

      Jiangyi Mao, Dan Wang, Shih-Hung Liu, Yandi Hang, Yaoyao Xu, Dr. Qiong Zhang, Dr. Wenjun Wu, Prof. Pi-Tai Chou and Prof. Jianli Hua

      Version of Record online: 18 OCT 2013 | DOI: 10.1002/ajoc.201300178

      Thumbnail image of graphical abstract

      To dye for: Three functionally separated donor-π-acceptor (D-π-A) sensitizers CP-IIII with a cyano group as the electron-accepting group and a pyridine as the anchoring group have been developed for dye-sensitized solar cells (DSSCs), in which the conversion efficiency for CP-II-based DSSCs achieves 4.02 %.

    4. Organic Electronics

      Charge-Transfer Nanostructures through Noncovalent Amphiphilic Self-Assembly: Extended Cofacial Donor-Acceptor Arrays (pages 161–169)

      Dr.  K. Venkata Rao, Krishnendu Jalani, K. Jayaramulu, Umesha Mogera, Dr. Tapas Kumar Maji and Dr. Subi J. George

      Version of Record online: 4 DEC 2013 | DOI: 10.1002/ajoc.201300229

      Thumbnail image of graphical abstract

      Build me up: Two mixed-stack charge-transfer (CT) nanostructures of perylene and tetrathiafulvalene donors with viologen acceptors were constructed by noncovalent amphiphilic self-assembly design. Irrespective of the viologens' morphology, CT amphiphiles self-assemble into 1D nanostructures and show impressive conductivity without any external doping.

    5. Photoluminescent Polymers

      Preparation and Photoinduced Energy and Electron Transfer of Donor-Silicon-Acceptor Polymers (pages 170–175)

      Joji Ohshita, Fumiya Kaneko, Daiki Tanaka and Yousuke Ooyama

      Version of Record online: 4 FEB 2014 | DOI: 10.1002/ajoc.201300288

      Thumbnail image of graphical abstract

      Free transfer: The photoluminescence properties of two polymers with donor-silicon-acceptor repeating units were investigated. One with bithiophene and diethynylbenzothiadiazole units as the donor and acceptor exhibits clear photoinduced electron transfer even in nonpolar cyclohexane. In contrast, for the other with more expanded π-conjugated units, terthiophene and dithienylbenzothiadiazole, only energy transfer occurred in cyclohexane.

    6. Dye-Sensitized Solar Cells

      Diphenyldibenzofulvene-Based Sensitizers for Efficient Dye-Sensitized Solar Cells: The Tuned Absorption Properties and Partially Suppressed Aggregation (pages 176–184)

      Huiyang Li, Runli Tang, Yingqin Hou, Yizhou Yang, Junnian Chen, Linfeng Liu, Prof. Hongwei Han, Prof.  Tianyou Peng, Prof.  Qianqian Li and Prof.  Zhen Li

      Version of Record online: 29 JAN 2014 | DOI: 10.1002/ajoc.201300231

      Thumbnail image of graphical abstract

      New organic sensitizers that contain a diphenyldibenzofulvene (DPDBF) bridge have been designed and synthesized to achieve an expanded system of conjugation and suppress possible intermolecular interactions. High conversion efficiencies were realized with the three new sensitizers, and LI-64, which contains the electron-donating SMe group as a substituent on the DPDBF unit, showed the best photovoltaic performance.

    7. Macrocyclic Dyads

      Macrocyclic Dyads Based on C60 and Perylenediimides Connected by Click Chemistry (pages 185–197)

      Sara Pla, Dr. Luis Martín-Gomis, Dr. Kei Ohkubo, Prof. Dr. Shunichi Fukuzumi, Prof. Dr. Fernando Fernández-Lázaro and Prof. Dr. Ángela Sastre-Santos

      Version of Record online: 16 JAN 2014 | DOI: 10.1002/ajoc.201300235

      Thumbnail image of graphical abstract

      Fuller surprises: Two perylenediimide (PDI)-[60]fullerene macrocyclic dyads connected through 1,2,3-triazole units have been synthesized and characterized. A small interaction between the C60 and PDI units in the ground state was detected by UV/vis and electrochemical measurements in both PDI-C60 cyclic systems. The occurrence of photoinduced energy-transfer processes between PDI and C60 were confirmed by time-resolved emission and transient absorption techniques.

    8. Charge Transfer

      Large π-Conjugated Chromophores Derived from Tetrathiafulvalene (pages 198–202)

      Dr. Hongpeng Jia, Dr. Jie Ding, Prof. Andreas Hauser, Prof. Silvio Decurtins and Dr. Shi-Xia Liu

      Version of Record online: 5 NOV 2013 | DOI: 10.1002/ajoc.201300144

      Thumbnail image of graphical abstract

      Make mine a large: The direct annulation of two dipyrido[3,2-a:2′,3′-c]phenazine units to a tetrathiafulvalene core leads to a large π-conjugate as a bridging ligand. Its coordination ability to transition-metal ions is exemplified by the formation of a stable dinuclear Ru2+ complex. The electrochemical, optical absorption, photoinduced intramolecular charge-transfer, and fluorescence characteristics of the ligand and the complex are described.

    9. Copper Sensors

      Synthesis, Characterization, and Sensing Behavior of an N-heteropentacene (pages 203–208)

      Dr. Gang Li, Dr. Junkuo Gao and Prof.Dr. Qichun Zhang

      Version of Record online: 11 DEC 2013 | DOI: 10.1002/ajoc.201300210

      Thumbnail image of graphical abstract

      Copper turned detective: An N-heteropentacene, 1,2,5,6-tetra(5-hexylthiophene-2-yl)-hexaazapentacene (4HP), was synthesized through one-step cyclocondensation reaction. The binding behavior of 4HP toward various metal cations was studied by UV/vis and fluorescence spectroscopy. 4HP demonstrated a selective and sensitive response towards Cu2+ ions, and the detection limit is 1.2 μM in N,N-dimethylformamide solution.

    10. Conjugated Polymers

      Tuning the Charge-Transport Property of Pyromellitic Diimide-Based Conjugated Polymers towards Efficient Field-Effect Transistors (pages 209–215)

      Xu Zhou, Yue Cao, Xiao-Ye Wang, Zi-Hao Guo, Dr.  Jie-Yu Wang and Prof.  Jian Pei

      Version of Record online: 27 JAN 2014 | DOI: 10.1002/ajoc.201300228

      Thumbnail image of graphical abstract

      More thiophene please! A series of donor-acceptor conjugated polymers were synthesized that include pyromellitic diimide (PMDI) as the acceptor and thiophene as the donor unit. With different thiophene/PMDI ratios in the polymer chains, the photophysical and electrochemical properties varied, and the field-effect transistors changed from n-type to ambipolar. Furthermore, with more thiophene, the hole mobilities of these polymers increased.

    11. Organogelators

      Multifunctional Photo- and Redox-Active Tetrathiafulvalene-based Organogelators: A Modular Approach (pages 216–224)

      Dr. David Canevet, Véronique Repussard and Prof. Dr. Marc Sallé

      Version of Record online: 4 FEB 2014 | DOI: 10.1002/ajoc.201300261

      Thumbnail image of graphical abstract

      Step by step: Organogelators are often serendipitously discovered and studies evaluating the role of each functional group in the gelation process are not so common. In this context, we show, through a modular approach, that the presence of both amide functions is critical in this gelator family and point out the potential of these tetrathiafulvalene-pyrene conjugates as molecular logic gates.

SEARCH

SEARCH BY CITATION