Photoexcitation dynamics and energy engineering in supramolecular doping of organic conjugated molecules

Xiang An; Chuanxin Wei; Lubing Bai; Jun Zhou; Le Wang; Yamin Han; Lili Sun; Jinyi Lin; Heyuan Liu; Jiewei Li; Man Xu; Haifeng Ling; Linghai Xie; Wei Huang

doi:10.1038/s41377-022-01062-6

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Photoexcitation dynamics and energy engineering in supramolecular doping of organic conjugated molecules

Original Articles

- Photoexcitation dynamics and energy engineering in supramolecular doping of organic conjugated molecules
- Light: Science & Applications Vol. 12, Issue 2, Pages: 183-193(2023)
- Affiliations：
  
  1.Key Laboratory of Flexible Electronics (KLOFE) & Institute of Advanced Materials (IAM), Nanjing Tech University (NanjingTech), 30 South Puzhu Road, Nanjing, 211816, China
  2.State Key Laboratory of Organic Electronics and Information Displays & Institute of Advanced Materials (IAM), Nanjing University of Posts & Telecommunications, 9 Wenyuan Road, Nanjing, 210023, China
  3.College of Science and Institute of New Energy, China University of Petroleum (East China), Qingdao, 266580, China
  4.Shaanxi Institute of Flexible Electronics (SIFE), Northwestern Polytechnical University (NPU), 127 West Youyi Road, Xi'an, 710072, Shaanxi, China
- Author bio：
  
  Jinyi Lin (iamjylin@njtech.edu.cn)
  Wei Huang (wei-huang@njtech.edu.cn)
- Funds：
- DOI：10.1038/s41377-022-01062-6
  CLC：
- Published：28 February 2023，
  
  Published Online：31 January 2023，
  
  Received：11 August 2022，
  
  Revised：15 December 2022，
  
  Accepted：15 December 2022
Scan for full text
An, X. et al. Photoexcitation dynamics and energy engineering in supramolecular doping of organic conjugated molecules. Light: Science & Applications, 12, 183-193 (2023).
DOI：

An, X. et al. Photoexcitation dynamics and energy engineering in supramolecular doping of organic conjugated molecules. Light: Science & Applications, 12, 183-193 (2023). DOI： 10.1038/s41377-022-01062-6.

摘要

Abstract

Doping and blending strategies are crucial means to precisely control the excited states and energy level in conjugated molecular systems. However

effective models and platforms are rarely proposed to systematically explore the effects of the formation of trapped doped centers on heterogeneous structures

energy level and ultrafast photophysical process. Herein

for deeply understanding the impact of molecular doping in film energy levels and photoexcitation dynamics

we set a supramolecular N-B coordination composed by the conjugated molecules of pyridine functionalized diarylfluorene (host material)

named as ODPF-Phpy and ODPF-(Phpy)

and the molecule of tris(perfluorophenyl)borane (BCF) (guest material). The generation of the molecular-level coordination bond increased the binding energy of N atoms and tuned the band-gap

leading to a new fluorescent emission center with longer excitation wavelength and emission wavelength. The intermolecular Förster resonance energy transfer (FRET) in blending films make it present inconsistent fluorescent behaviors compared to that in solution. The charge transfer (CT) state of N-B coordinated compounds and the changed dielectric constant of blending films resulted in a large PL spectra red-shift with the increased dopant ratio

causing a wide-tunable fluorescent color. The excited state behaviors of two compounds in blending system was further investigated by the transient absorption (TA) spectroscopy. Finally

we found supramolecular coordination blending can effectively improve the films' photoluminescence quantum yield (PLQY) and conductivity. We believe this exploration in the internal coordination mechanisms would deepen the insights about doped semiconductors and is helpful in developing novel high-efficient fluorescent systems.

关键词

Keywords

references

R. Kabe , C. Adachi . Organic long persistent luminescence . Nature , 2017 . 550 384 -387 . DOI:10.1038/nature24010http://doi.org/10.1038/nature24010 .

K. Goushi , 等 . Organic light-emitting diodes employing efficient reverse intersystem crossing for triplet-to-singlet state conversion . Nat. Photonics , 2012 . 6 253 -258 . DOI:10.1038/nphoton.2012.31http://doi.org/10.1038/nphoton.2012.31 .

D. H. Kim , 等 . High-efficiency electroluminescence and amplified spontaneous emission from a thermally activated delayed fluorescent near-infrared emitter . Nat. Photonics , 2018 . 12 98 -104 . DOI:10.1038/s41566-017-0087-yhttp://doi.org/10.1038/s41566-017-0087-y .

X. H. Jin , 等 . Long-range exciton transport in conjugated polymer nanofibers prepared by seeded growth . Science , 2018 . 360 897 -900 . DOI:10.1126/science.aar8104http://doi.org/10.1126/science.aar8104 .

A. T. Haedler , 等 . Long-range energy transport in single supramolecular nanofibres at room temperature . Nature , 2015 . 523 196 -199 . DOI:10.1038/nature14570http://doi.org/10.1038/nature14570 .

J. Y. Lin , 等 . Ultrastable supramolecular self-encapsulated wide-bandgap conjugated polymers for large-area and flexible electroluminescent devices . Adv. Mater. , 2019 . 31 1804811 DOI:10.1002/adma.201804811http://doi.org/10.1002/adma.201804811 .

X. An , 等 . Long-range ordered hierarchical structure assisted by the side-oligoether network in light-emitting conjugated polymer for an efficient deep-blue organic laser . Chem. Mater. , 2021 . 33 5326 -5336 . DOI:10.1021/acs.chemmater.1c01359http://doi.org/10.1021/acs.chemmater.1c01359 .

T. K. Zhang , 等 . Ion-modulated radical doping of spiro-OMeTAD for more efficient and stable perovskite solar cells . Science , 2022 . 377 495 -501 . DOI:10.1126/science.abo2757http://doi.org/10.1126/science.abo2757 .

O. P. Dimitriev , N. V. Lavrik . Suppression of conductivity in polyaniline films in presence of pentadecyl-tetracyanoquinodimethane . Synth. Met. , 1999 . 98 173 -175 . DOI:10.1016/S0379-6779(98)00158-1http://doi.org/10.1016/S0379-6779(98)00158-1 .

I. E. Jacobs , A. J. Moulé . Controlling molecular doping in organic semiconductors . Adv. Mater. , 2017 . 29 1703063 DOI:10.1002/adma.201703063http://doi.org/10.1002/adma.201703063 .

Y. Karpov , 等 . High conductivity in molecularly p-doped diketopyrrolopyrrole-based polymer: the impact of a high dopant strength and good structural order . Adv. Mater. , 2016 . 28 6003 -6010 . DOI:10.1002/adma.201506295http://doi.org/10.1002/adma.201506295 .

W. Y. Lei , 等 . Black phosphorus nanostructures: recent advances in hybridization, doping and functionalization . Chem. Soc. Rev. , 2017 . 46 3492 -3509 . DOI:10.1039/C7CS00021Ahttp://doi.org/10.1039/C7CS00021A .

C. Y. Yang , 等 . Enhancing the n-type conductivity and thermoelectric performance of donor-acceptor copolymers through donor engineering . Adv. Mater. , 2018 . 30 1802850 DOI:10.1002/adma.201802850http://doi.org/10.1002/adma.201802850 .

G. H. Kim , 等 . Engineered doping of organic semiconductors for enhanced thermoelectric efficiency . Nat. Mater. , 2013 . 12 719 -723 . DOI:10.1038/nmat3635http://doi.org/10.1038/nmat3635 .

D. Kiefer , 等 . Double doping of conjugated polymers with monomer molecular dopants . Nat. Mater. , 2019 . 18 149 -155 . DOI:10.1038/s41563-018-0263-6http://doi.org/10.1038/s41563-018-0263-6 .

X. Lin , 等 . Beating the thermodynamic limit with photo-activation of n-doping in organic semiconductors . Nat. Mater. , 2017 . 16 1209 -1215 . DOI:10.1038/nmat5027http://doi.org/10.1038/nmat5027 .

N. Sakai , 等 . Adduct-based p-doping of organic semiconductors . Nat. Mater. , 2021 . 20 1248 -1254 . DOI:10.1038/s41563-021-00980-xhttp://doi.org/10.1038/s41563-021-00980-x .

J. Y. Lin , 等 . Heteroatomic conjugated polymers and the spectral tuning of electroluminescence via a supramolecular coordination strategy . Macromol. Rapid Commun. , 2016 . 37 1807 -1813 . DOI:10.1002/marc.201600445http://doi.org/10.1002/marc.201600445 .

H. H. Lu , 等 . Self-dopant formation in poly(9, 9-di-n-octylfluorene) via a dipping method for efficient and stable pure-blue electroluminescence . Adv. Mater. , 2007 . 19 2574 -2579 . DOI:10.1002/adma.200602632http://doi.org/10.1002/adma.200602632 .

J. Y. Lin , 等 . A rational molecular design of β-phase polydiarylfluorenes: synthesis, morphology, and organic lasers . Macromolecules , 2014 . 47 1001 -1007 . DOI:10.1021/ma402585nhttp://doi.org/10.1021/ma402585n .

P. Pingel , 等 . p-Type doping of poly(3-hexylthiophene) with the strong lewis acid tris(pentafluorophenyl)borane . Adv. Electron. Mater. , 2016 . 2 1600204 DOI:10.1002/aelm.201600204http://doi.org/10.1002/aelm.201600204 .

K. Ortstein , 等 . Band gap engineering in blended organic semiconductor films based on dielectric interactions . Nat. Mater. , 2021 . 20 1407 -1413 . DOI:10.1038/s41563-021-01025-zhttp://doi.org/10.1038/s41563-021-01025-z .

B. Yurash , 等 . Towards understanding the doping mechanism of organic semiconductors by Lewis acids . Nat. Mater. , 2019 . 18 1327 -1334 . DOI:10.1038/s41563-019-0479-0http://doi.org/10.1038/s41563-019-0479-0 .

J. Y. Oh , 等 . Intrinsically stretchable and healable semiconducting polymer for organic transistors . Nature , 2016 . 539 411 -415 . DOI:10.1038/nature20102http://doi.org/10.1038/nature20102 .

H. Y. Chen , 等 . Polymer solar cells with enhanced open-circuit voltage and efficiency . Nat. Photonics , 2009 . 3 649 -653 . DOI:10.1038/nphoton.2009.192http://doi.org/10.1038/nphoton.2009.192 .

B. G. Kim , 等 . A molecular design principle of lyotropic liquid-crystalline conjugated polymers with directed alignment capability for plastic electronics . Nat. Mater. , 2013 . 12 659 -664 . DOI:10.1038/nmat3595http://doi.org/10.1038/nmat3595 .

L. H. Xie , 等 . Polyfluorene-based semiconductors combined with various periodic table elements for organic electronics . Prog. Polym. Sci. , 2012 . 37 1192 -1264 . DOI:10.1016/j.progpolymsci.2012.02.003http://doi.org/10.1016/j.progpolymsci.2012.02.003 .

W. Huang , 等 . A new blue light-emitting polymer containing substituted thiophene and an arylene-1, 3, 4-oxadiazole moiety . Adv. Mater. , 1998 . 10 593 -596 . DOI:10.1002/(SICI)1521-4095(199805)10:8<593::AID-ADMA593>3.0.CO;2-9http://doi.org/10.1002/(SICI)1521-4095(199805)10:8<593::AID-ADMA593>3.0.CO;2-9 .

W. L. Yu , 等 . Tuning redox behavior and emissive wavelength of conjugated polymers by p−n diblock structures . J. Am. Chem. Soc. , 1998 . 120 11808 -11809 . DOI:10.1021/ja982561khttp://doi.org/10.1021/ja982561k .

J. Yuan , 等 . Reducing voltage losses in the A-DA'D-A acceptor-based organic solar cells . Chem , 2020 . 6 2147 -2161 . DOI:10.1016/j.chempr.2020.08.003http://doi.org/10.1016/j.chempr.2020.08.003 .

Y. Han , 等 . Doping of large ionization potential indenopyrazine polymers via lewis acid complexation with tris(pentafluorophenyl)borane: a simple method for improving the performance of organic thin-film transistors . Chem. Mater. , 2016 . 28 8016 -8024 . DOI:10.1021/acs.chemmater.6b03761http://doi.org/10.1021/acs.chemmater.6b03761 .

J. Y. Lin , 等 . Supramolecular polymer-molecule complexes as gain media for ultraviolet lasers . ACS Macro Lett. , 2016 . 5 967 -971 . DOI:10.1021/acsmacrolett.6b00394http://doi.org/10.1021/acsmacrolett.6b00394 .

G. C. Welch , G. C. Bazan . Lewis acid adducts of narrow band gap conjugated polymers . J. Am. Chem. Soc. , 2011 . 133 4632 -4644 . DOI:10.1021/ja110968mhttp://doi.org/10.1021/ja110968m .

T. Mori , Y. Yoshigoe , Y. Kuninobu . Control of multicolor and white emission by adjusting the equilibrium between fluorophores, lewis acids, and their complexes in polymers . Angew. Chem. Int. Ed. , 2019 . 58 14457 -14461 . DOI:10.1002/anie.201903408http://doi.org/10.1002/anie.201903408 .

M. M. Hansmann , 等 . B(C6F5)3: a lewis acid that brings the light to the solid state . Angew. Chem. Int. Ed. , 2016 . 55 1196 -1199 . DOI:10.1002/anie.201508461http://doi.org/10.1002/anie.201508461 .

T. Ono , M. Sugimoto , Y. Hisaeda . Multicomponent molecular puzzles for photofunction design: emission color variation in Lewis acid-base pair crystals coupled with guest-to-host charge transfer excitation . J. Am. Chem. Soc. , 2015 . 137 9519 -9522 . DOI:10.1021/jacs.5b04178http://doi.org/10.1021/jacs.5b04178 .

S. Q. Ma , 等 . Direct observation of the symmetrical and asymmetrical protonation states in molecular crystals . J. Phys. Chem. Lett. , 2017 . 8 3068 -3072 . DOI:10.1021/acs.jpclett.7b01454http://doi.org/10.1021/acs.jpclett.7b01454 .

E. Raymundo-Piñero , 等 . Structural characterization of N-containing activated carbon fibers prepared from a low softening point petroleum pitch and a melamine resin . Carbon , 2002 . 40 597 -608 . DOI:10.1016/S0008-6223(01)00155-5http://doi.org/10.1016/S0008-6223(01)00155-5 .

J. W. Li , 等 . From dark TICT state to emissive quasi-TICT state: the AIE mechanism of N-(3-(benzo[d]oxazol-2-yl)phenyl)-4-tert-butylbenzamide . J. Phys. Chem. C. , 2015 . 119 2133 -2141 . DOI:10.1021/jp5089433http://doi.org/10.1021/jp5089433 .

C. Sun , 等 . Boosting the stimulated emission properties of host: guest polymer blends by inserting chain twists in the host polymer . Adv. Funct. Mater. , 2022 . 32 2206723 DOI:10.1002/adfm.202206723http://doi.org/10.1002/adfm.202206723 .

J. Cabanillas-Gonzalez , G. Grancini , G. Lanzani . Pump-probe spectroscopy in organic semiconductors: monitoring fundamental processes of relevance in optoelectronics . Adv. Mater. , 2011 . 23 5468 -5485 . DOI:10.1002/adma.201102015http://doi.org/10.1002/adma.201102015 .

Y. M. Han , 等 . Deep-blue thiophene-based steric oligomers as a low-threshold laser gain and host material . Adv. Optical Mater. , 2020 . 8 1902163 DOI:10.1002/adom.201902163http://doi.org/10.1002/adom.201902163 .

C. Y. Chan , 等 . Stable pure-blue hyperfluorescence organic light-emitting diodes with high-efficiency and narrow emission . Nat. Photonics , 2021 . 15 203 -207 . DOI:10.1038/s41566-020-00745-zhttp://doi.org/10.1038/s41566-020-00745-z .

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