Charge-Transfer Emission of Mixed Organic Cocrystal Microtubes over the Whole Composition Range

A series of crystalline mixed cocrystal microtubes comprising organic charge-transfer (CT) complexes has been prepared. The emission colors of the mixed cocrystal microtubes can be tailored from green to orange at low dopant concentrations (0 < x ⩽ 5%), while their hexagonal cross sections can transform into square ones gradually at higher concentrations (0.15 < x < 1). In addition, we can further extend the solvent-processed synthetic route to other CT pairs based on structural compatibility consideration.

[1]  Daoben Zhu,et al.  Fullerene/sulfur-bridged annulene cocrystals: two-dimensional segregated heterojunctions with ambipolar transport properties and photoresponsivity. , 2013, Journal of the American Chemical Society.

[2]  Gang Li,et al.  Achieving High‐Efficiency Polymer White‐Light‐Emitting Devices , 2006 .

[3]  D. Perepichka,et al.  Crystal engineering of dual channel p/n organic semiconductors by complementary hydrogen bonding. , 2014, Angewandte Chemie.

[4]  Daniel Moses,et al.  Multilayer Polymer Light‐Emitting Diodes: White‐Light Emission with High Efficiency , 2005 .

[5]  E. W. Meijer,et al.  Multicolour self-assembled fluorene co-oligomers: from molecules to the solid state via white-light-emitting organogels. , 2009, Chemistry.

[6]  S. Forrest,et al.  Highly efficient phosphorescent emission from organic electroluminescent devices , 1998, Nature.

[7]  Daoben Zhu,et al.  Sulfur‐Bridged Annulene‐TCNQ Co‐Crystal: A Self‐Assembled ‘‘Molecular Level Heterojunction’’ with Air Stable Ambipolar Charge Transport Behavior , 2012, Advanced materials.

[8]  Kangwon Lee,et al.  Activating efficient phosphorescence from purely organic materials by crystal design. , 2011, Nature chemistry.

[9]  F. Marumo,et al.  The crystal structure of the 1:1 complex of anthracene and 1,2,4,5‐tetracyanobenzene , 1972 .

[10]  Gautam R. Desiraju,et al.  Supramolecular Synthons in Crystal Engineering—A New Organic Synthesis , 1995 .

[11]  K. V. Rao,et al.  Highly Pure Solid‐State White‐Light Emission from Solution‐Processable Soft‐Hybrids , 2013, Advanced materials.

[12]  R. Al‐Kaysi,et al.  Formation of Cocrystal Nanorods by Solid-State Reaction of Tetracyanobenzene in 9-Methylanthracene Molecular Crystal Nanorods , 2009 .

[13]  C. Schäfer,et al.  White-light-emitting self-assembled nanofibers and their evidence by microspectroscopy of individual objects. , 2011, Journal of the American Chemical Society.

[14]  S. Bhattacharya,et al.  Unusual salt-induced color modulation through aggregation-induced emission switching of a bis-cationic phenylenedivinylene-based π hydrogelator. , 2012, Chemistry.

[15]  J. Yao,et al.  Cooperative assembly of binary molecular components into tubular structures for multiple photonic applications. , 2011, Angewandte Chemie.

[16]  N. Mataga,et al.  Electron donor-acceptor interactions in the fluorescent state of tetracyanobenzene-aromatic hydrocarbon complexes , 1969 .

[17]  Reji Varghese,et al.  White-light-emitting DNA (WED). , 2009, Chemistry.

[18]  J. Pei,et al.  One‐Dimensional Microwires Formed by the Co‐Assembly of Complementary Aromatic Donors and Acceptors , 2009 .

[19]  R. Dillon,et al.  The effects of photochemical and mechanical damage on the excited state dynamics of charge-transfer molecular crystals composed of tetracyanobenzene and aromatic donor molecules. , 2011, The journal of physical chemistry. A.

[20]  Stephen R. Forrest,et al.  Management of singlet and triplet excitons for efficient white organic light-emitting devices , 2006, Nature.

[21]  M. Yamashita,et al.  Enhancement of luminescence intensity in TMPY/perylene co-single crystals , 2011 .

[22]  M. Kuz’min,et al.  Luminescence of crystalline complexes of tetracyanobenzene with aromatic hydrocarbons , 1977 .

[23]  N. Armaroli,et al.  White-light-emitting supramolecular gels. , 2014, Angewandte Chemie.

[24]  Subi J. George,et al.  MOF Nano‐Vesicles and Toroids: Self‐Assembled Porous Soft‐Hybrids for Light Harvesting , 2013 .

[25]  Shui-Tong Lee,et al.  White‐Light Emitting Microtubes of Mixed Organic Charge‐Transfer Complexes , 2012, Advanced materials.

[26]  D. Ramaiah,et al.  DNA-assisted white light emission through FRET. , 2011, Chemical communications.

[27]  G. Day,et al.  A cocrystal strategy to tune the luminescent properties of stilbene-type organic solid-state materials. , 2011, Angewandte Chemie.

[28]  A. Ajayaghosh,et al.  RGB Emission through Controlled Donor Self‐Assembly and Modulation of Excitation Energy Transfer: A Novel Strategy to White‐Light‐Emitting Organogels , 2009 .

[29]  W. Jin,et al.  Cocrystals assembled by pyrene and 1,2- or 1,4-diiodotetrafluorobenzenes and their phosphorescent behaviors modulated by local molecular environment , 2012 .

[30]  Oh Kyu Kwon,et al.  Tailor-made highly luminescent and ambipolar transporting organic mixed stacked charge-transfer crystals: an isometric donor-acceptor approach. , 2013, Journal of the American Chemical Society.

[31]  J. Wuest,et al.  Molecular solids: Co-crystals give light a tune-up. , 2012, Nature chemistry.

[32]  Jiaxing Huang,et al.  Wire-on-wire growth of fluorescent organic heterojunctions. , 2012, Journal of the American Chemical Society.

[33]  K. Yager,et al.  A supramolecular complex in small-molecule solar cells based on contorted aromatic molecules. , 2012, Angewandte Chemie.