Molecular Design Principles for Near-Infrared Absorbing and Emitting Indolizine Dyes.

Desirable components for dye-sensitzed solar cell (DSC) sensitizers and fluorescent imaging dyes include strong donating building blocks coupled with well-balanced acceptor functionalities for absorption beyond the visible range. We have evaluated the effects of increasing acceptor strengths and incorporation of dye morphology controlling groups on molar absorptivity and absorption breadth with indolizine donor-based dyes. Indolizine-based D-A and D-π-A sensitizers incorporating bis-rhodanine, tricyanofuran (TCF), and cyanoacrylic acid functionalities were analyzed for performance in DSC devices. The TCF derivatives were also evaluated as near-infrared (NIR)-emissive materials with the AH25 emissions extending past 1000 nm.

[1]  Shuo Diao,et al.  Traumatic Brain Injury Imaging in the Second Near‐Infrared Window with a Molecular Fluorophore , 2016, Advanced materials.

[2]  J. Teuscher,et al.  Blue-Coloured Highly Efficient Dye-Sensitized Solar Cells by Implementing the Diketopyrrolopyrrole Chromophore , 2013, Scientific Reports.

[3]  Mingfei Xu,et al.  The structure–property relationship of organic dyes in mesoscopic titania solar cells: only one double-bond difference , 2011 .

[4]  M. Grätzel,et al.  Meso-substituted porphyrins for dye-sensitized solar cells. , 2014, Chemical reviews.

[5]  Shufang Zhang,et al.  Highly efficient dye-sensitized solar cells: progress and future challenges , 2013 .

[6]  M. Alpers Published online: , 2001 .

[7]  Kenji Kakiage,et al.  Highly-efficient dye-sensitized solar cells with collaborative sensitization by silyl-anchor and carboxy-anchor dyes. , 2015, Chemical communications.

[8]  Thieno[3,4-b]pyrazine as an Electron Deficient π-Bridge in D-A-π-A DSCs. , 2016, ACS applied materials & interfaces.

[9]  M. Fischer,et al.  Metallfreie organische Farbstoffe für farbstoffsensibilisierte Solarzellen – von Struktur‐Eigenschafts‐Beziehungen zu Designregeln , 2009 .

[10]  Gregory S. Tschumper,et al.  Indolizine‐Based Donors as Organic Sensitizer Components for Dye‐Sensitized Solar Cells , 2015 .

[11]  M. Grätzel,et al.  Modulating dye E(S+/S*) with efficient heterocyclic nitrogen containing acceptors for DSCs. , 2012, Chemical communications.

[12]  Gregory S. Tschumper,et al.  A Computational and Experimental Study of Thieno[3,4-b]thiophene as a Proaromatic π-Bridge in Dye-Sensitized Solar Cells. , 2016, Chemistry.

[13]  Kinetics of Iodine-Free Redox Shuttles in Dye-Sensitized Solar Cells: Interfacial Recombination and Dye Regeneration. , 2015, Accounts of chemical research.

[14]  Weihong Zhu,et al.  Insight into D-A-π-A Structured Sensitizers: A Promising Route to Highly Efficient and Stable Dye-Sensitized Solar Cells. , 2015, ACS applied materials & interfaces.

[15]  Hidetoshi Miura,et al.  High-conversion-efficiency organic dye-sensitized solar cells with a novel indoline dye. , 2008, Chemical communications.

[16]  M. Grätzel,et al.  Solid‐State Dye‐Sensitized Solar Cells Using a Novel Class of Ullazine Dyes as Sensitizers , 2013 .

[17]  M. C. Mancini,et al.  Bioimaging: second window for in vivo imaging. , 2009, Nature nanotechnology.

[18]  M. Grätzel,et al.  The molecular engineering of organic sensitizers for solar-cell applications. , 2013, Angewandte Chemie.

[19]  A. Hagfeldt,et al.  Efficient near infrared D-pi-A sensitizers with lateral anchoring group for dye-sensitized solar cells. , 2009, Chemical communications.

[20]  Jie Zhang,et al.  N-annulated perylene as an efficient electron donor for porphyrin-based dyes: enhanced light-harvesting ability and high-efficiency Co(II/III)-based dye-sensitized solar cells. , 2014, Journal of the American Chemical Society.

[21]  Michael Grätzel,et al.  A new generation of platinum and iodine free efficient dye-sensitized solar cells. , 2012, Physical chemistry chemical physics : PCCP.

[22]  Peng Wang,et al.  A metal-free N-annulated thienocyclopentaperylene dye: power conversion efficiency of 12% for dye-sensitized solar cells. , 2015, Angewandte Chemie.

[23]  H. Minoura,et al.  Novel thiophene-conjugated indoline dyes for zinc oxide solar cells , 2009 .

[24]  Junle Qu,et al.  Super-resolution fluorescent materials: an insight into design and bioimaging applications. , 2016, Chemical Society reviews.

[25]  T. Sajoto,et al.  The role of π bridges in high-efficiency DSCs based on unsymmetrical squaraines. , 2013, Chemistry.

[26]  Shuo Diao,et al.  A small-molecule dye for NIR-II imaging. , 2016, Nature materials.

[27]  Basile F. E. Curchod,et al.  Dye-sensitized solar cells with 13% efficiency achieved through the molecular engineering of porphyrin sensitizers. , 2014, Nature chemistry.

[28]  Mohammad Khaja Nazeeruddin,et al.  Near-infrared sensitization of solid-state dye-sensitized solar cells with a squaraine dye , 2012 .

[29]  M. Grätzel,et al.  A low-cost, high-efficiency solar cell based on dye-sensitized colloidal TiO2 films , 1991, Nature.

[30]  T. Brinck,et al.  Tuning the HOMO and LUMO energy levels of organic chromophores for dye sensitized solar cells. , 2007, The Journal of organic chemistry.

[31]  Henry J. Snaith,et al.  The renaissance of dye-sensitized solar cells , 2012, Nature Photonics.

[32]  Kenji Kakiage,et al.  Fabrication of a high-performance dye-sensitized solar cell with 12.8% conversion efficiency using organic silyl-anchor dyes. , 2015, Chemical communications.

[33]  M. Fischer,et al.  Metal-free organic dyes for dye-sensitized solar cells: from structure: property relationships to design rules. , 2009, Angewandte Chemie.

[34]  U. Rothlisberger,et al.  Synthesis, characterization and ab initio investigation of a panchromatic ullazine–porphyrin photosensitizer for dye-sensitized solar cells , 2016 .

[35]  A low recombination rate indolizine sensitizer for dye-sensitized solar cells. , 2016, Chemical communications.

[36]  N. Hammer,et al.  Donor–Acceptor–Donor Thienopyrazines via Pd-Catalyzed C–H Activation as NIR Fluorescent Materials , 2015, The Journal of organic chemistry.

[37]  Kenji Kakiage,et al.  An achievement of over 12 percent efficiency in an organic dye-sensitized solar cell. , 2014, Chemical communications.

[38]  M. Zhang,et al.  Dithienopicenocarbazole as the kernel module of low-energy-gap organic dyes for efficient conversion of sunlight to electricity , 2015 .

[39]  Chia‐Yuan Chen,et al.  Unsymmetrical squaraines incorporating quinoline for near infrared responsive dye-sensitized solar cells. , 2012, Organic letters.