Photosynergetic Responses in Molecules and Molecular Aggregates

586 Pages·2020·33.235 MB·English

by  Hiroshi Miyasaka, Kenji Matsuda, Jiro Abe, Tsuyoshi Kawai

Hiroshi Miyasaka · Kenji Matsuda ·
Jiro Abe · Tsuyoshi Kawai Editors
Photosynergetic
Responses in
Molecules and
Molecular Aggregates
Photosynergetic Responses in Molecules
and Molecular Aggregates
Hiroshi Miyasaka Kenji Matsuda
(cid:129) (cid:129)
Jiro Abe Tsuyoshi Kawai
(cid:129)
Editors
Photosynergetic Responses
in Molecules and Molecular
Aggregates
123
Editors
Hiroshi Miyasaka KenjiMatsuda
Graduate Schoolof Engineering Science Graduate Schoolof Engineering
Osaka University KyotoUniversity
Toyonaka,Osaka, Japan Kyoto, Japan
Jiro Abe TsuyoshiKawai
Department ofChemistry Graduate Schoolof Materials Science
Aoyama GakuinUniversity Nara Institute of Science andTechnology
Sagamihara, Kanagawa, Japan Ikoma, Nara,Japan
ISBN978-981-15-5450-6 ISBN978-981-15-5451-3 (eBook)
https://doi.org/10.1007/978-981-15-5451-3
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Preface
Molecules in the electronic excited state take important roles in various processes.
For the excited molecules in condensed phase, however, there exist general
restrictions in the efficient utilization of light energies. First, higher electronically
excitedstatesofratherlargemolecules veryrapidlyrelaxtolowerelectronicstates
(Kasha’s rule), and some portion of the photon energy is diminished in this
relaxation.Second,alargenumberofthemolecules excitedinassembliesundergo
fast annihilation, and only a small number of excited state molecules can remain,
leadingtothelossofthenumberofphotonsabsorbedinthesystem.Inaddition,the
electronicstateaccessiblebythephotoabsorptionislimitedbytheopticalselection
rule, and we cannot access various dark electronic excited states of molecules.
These restrictions have confined most of the photochemical responses into the
frameworkof“one-photonandone-moleculeoutcomesinthelowestexcitedstate”
and have been preventing us from efficiently and cooperatively utilizing a number
of photons and excited molecules.
To explore principles to realize responses induced by a number of photons and
excitedmolecules(photosynergeticresponses)beyondthelimitof“one-photonand
one-molecule outcomes in the lowest excited state” leading to the new paradigm,
we organized a Grant-in-Aid for Scientific Research (Kakenhi) Project on
Innovative Areas “Photosynergetics: Application of Cooperative Excitation into
Innovative Molecular Systems with High-Order Photofunctions” (Hiroshi
Miyasaka,projectleaderand34researchgroups)from2014to2019,supportedby
the Ministry of Education, Culture, Sports, Science and Technology, Japan.
The research project focused on the three subjects for the realization of the
photosynergetic responses.
(1) Exploration and elucidation of reactions from higher electronic excited states,
modulation of electronic states by the local field and effective utilization of
multiple excitons.
(2) Development of high-order photofunctions based on the synergetic action of
photoresponsive molecules.
v
vi Preface
(3) Advancedconstructionofmeso-andmacroscopiccooperativephotoresponsive
molecular assemblies and elucidation of their mechanisms.
This book compiles the accomplishments of this research project conducted with
thesesubjects.InPartI,weintroducetheresearchresultsofthefirstsubjectdirectly
relating to the three general restrictions. By developing and applying multiple and
multiphoton excitations, nano-environments, new materials and theoretical meth-
ods, we could find new phenomena beyond the three restrictions and elucidated
their mechanisms, which can lead to the realization of photosynergetic responsive
materials.Inaddition,thedevelopmentsofnewmaterials,experimentalapparatuses
and theoretical methods in the study have ensured further progress of the research
field on the photosynergetics.
Part II bundles research outcomes on the second subject aiming to explore
photoresponsivesystemswherethephotoreactioninamolecularlevelisintegrated
and amplified. By designing and synthesizing molecules and assemblies, reaction
chains and molecular networks overcoming the loss of the photon energy were
achieved by the amplification. Moreover, many examples were realized for coop-
erative photoresponses of molecular aggregates arising from the integration of
molecularphotoreactions.Fromtheseresults,wecouldobtaintheprinciplesforthe
realization of responses through the multiple photons and multiple excited mole-
cules, which can guide future research.
Part III compiles the photoresponse of materials in rather large scale, where the
individualreactionofmoleculesintheexcitedstateisaccumulatedinthematerial,
leading to the hierarchical photoresponse of meso- and macroscopic materials.
Researchers in various fields of materials chemistry such as molecular synthesis,
designing of molecular crystals, time- and space-resolved detection of reaction
dynamics developed photoresponsive meso- and macroscopic systems and eluci-
dated their mechanisms. These new phenomena, materials, mechanisms and
experimental methods can lead to the further advancement of photosynergetics.
We hope that the achievement of the project is a significant landmark and
principles in the stream of studies on the photochemistry of molecules and
materials.
Theeditorsexpresstheirsincere appreciationtooutstandingcontributors andto
the Ministry of Education, Culture, Sports, Science and Technology, Japan, for
their support of the project.
Toyonaka, Japan Hiroshi Miyasaka
Kyoto, Japan Kenji Matsuda
Sagamihara, Japan Jiro Abe
Ikoma, Japan Tsuyoshi Kawai
Contents
Part I Exploration and Elucidation of Reactions from Higher
Electronic Excited States, Modulation of Electronic States
by the Local Field, and Effective Utilization of Multiple
Excitons
1 Advanced Control of Photochemical Reactions Leading
to Synergetic Responses in Molecules and Mesoscopic
Materials. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 3
Hiroshi Miyasaka, Hikaru Sotome, and Syoji Ito
2 Advanced Electronic Structure Theory for High-Accuracy
Prediction of Higher Excited States and Its Application
to Photochromic Molecules . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 29
Takeshi Yanai
3 Enhanced and Selective Two-Photon Excitation of Molecular
Vibronic States Using Entangled Photons. . . . . . . . . . . . . . . . . . . . 43
Hisaki Oka
4 Stepwise Two-Photon Photochromism. . . . . . . . . . . . . . . . . . . . . . . 57
Jiro Abe, Yoichi Kobayashi, and Katsuya Mutoh
5 Suppression of Internal Conversions from Pseudo-Degenerate
Excited Electronic States. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 79
Wataru Ota and Tohru Sato
6 Advanced Function Control of Photochemical Reactions
Using Mesoscopic Structures. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 93
Keisuke Imaeda and Kohei Imura
7 Plasmon-Associated Control of Chemical Reaction
at Nanometer Scale. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 117
Shuichi Toyouchi, Tomoko Inose, Kenji Hirai, and Hiroshi Uji-i
vii
viii Contents
8 Modulations of Electronic States in Plasmonic Strong Coupling
Systems and Their Application to Photochemical
Reaction Fields . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 135
Kosei Ueno
9 Photosynergetic Effects on Triplet–Triplet Annihilation
Upconversion Processes in Solid Studied by Theory
and Experiments. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 147
Kenji Kamada, Ryuma Sato, Toshiko Mizokuro,
Hirotaka Kito-Nishioka, and Yasuteru Shigeta
10 Hot Carrier Transfer and Carrier Manipulation
of Semiconductor Nanocrystals. . . . . . . . . . . . . . . . . . . . . . . . . . . . 171
Naoto Tamai and Sadahiro Masuo
11 The Confinement and Migration of Charge-Carriers in Lead
Halide Perovskites. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 197
Sushant Ghimire, Lata Chouhan, and Vasudevanpillai Biju
12 Plasmon-Induced Carrier Transfer for Infrared Light
Energy Conversion . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 211
Masanori Sakamoto, Zichao Lian, and Toshiharu Teranishi
13 Controlling Optical Properties of Multinary Quantum Dots
for Developing Novel Photoelectrochemical Reactions. . . . . . . . . . . 223
Tsukasa Torimoto and Tatsuya Kameyama
Part II Development of High-Order Photofunctions Based
on Synergetic Action of Photoresponsive Molecules
14 Photosynergetic Enhancement of Photosensitivity
of Photochromic Terarylenes . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 241
Tsuyoshi Kawai
15 Creation of Molecularly Integrated Multi-responsive
Photochromic Systems . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 253
Yasushi Yokoyama
16 Efficient Singlet Fission in Acene-Based Molecular Assemblies. . . . 275
Taku Hasobe
17 Synergetic Photon Upconversion Realized by a Controlled
Toroidal Interaction in Hexaarylbenzene Derivatives . . . . . . . . . . . 287
Tadashi Mori
18 p-Electronic Ion-Pairing Assemblies for Photoswitching
Materials. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 301
Yohei Haketa, Ryohei Yamakado, Kazuki Urakawa,
and Hiromitsu Maeda
Contents ix
19 Photoinduced Morphological Transformation and Photodriven
Movement of Objects Using Self-assembly of Amphiphilic
Diarylethene in Water. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 327
Kenji Higashiguchi and Kenji Matsuda
20 Functional Photoactive Materials Based on Flexible
p Molecules. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 349
Shohei Saito
21 Giant Amplification of Fluorescence Quenching in Photochromic
Nanoparticles and Crystals. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 361
Tuyoshi Fukaminato, Sanae Ishida, Jia Su, Keitaro Nakatani,
and Rémi Métivier
22 Cooperative Molecular Alignment Process Enabled by Scanning
Wave Photopolymerization . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 375
Atsushi Shishido, Yoshiaki Kobayashi, Norihisa Akamatsu,
Kyohei Hisano, and Miho Aizawa
23 Ultrafast Energy Transfer of Biohybrid Photosynthetic Antenna
Complexes in Molecular Assembly Systems . . . . . . . . . . . . . . . . . . 389
Takehisa Dewa, Yusuke Yoneda, Masaharu Kondo,
Hiroshi Miyasaka, and Yutaka Nagasawa
Part III Advanced Construction of Meso- and Macroscopic
Cooperative Photoresponsive Molecular Assemblies
and Elucidation of Their Mechanisms
24 Biomimetic Functions by Microscopic Molecular Reactions
in Macroscopic Photoresponsive Crystalline System . . . . . . . . . . . . 405
Kingo Uchida, Ryo Nishimura, Hiroyuki Mayama,
Tsuyoshi Tsujioka, Satoshi Yokojima, and Shinichiro Nakamura
25 Photoresponsive Molecular Crystals for Light-Driven
Photoactuators . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 427
Seiya Kobatake and Daichi Kitagawa
26 Interplay of Photoisomerization and Phase Transition Events
Provide a Working Supramolecular Motor. . . . . . . . . . . . . . . . . . . 449
Yoshiyuki Kageyama
27 CrawlingandBendingMotionsofAzobenzeneDerivativesBased
on Photoresponsive Solid–Liquid Phase Transition System. . . . . . . 465
Yasuo Norikane, Koichiro Saito, and Youfeng Yue
28 Photomechanical Effects in Crosslinked Liquid-Crystalline
Polymers with Photosynergetic Processes . . . . . . . . . . . . . . . . . . . . 479
Toru Ube and Tomiki Ikeda
x Contents
29 Femtosecond Pump-Probe Microspectroscopy
and Its Application to Single Organic Nanoparticles
and Microcrystals . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 493
Yukihide Ishibashi and Tsuyoshi Asahi
30 Single-Molecule Level Study and Control of Collective
Photoresponse in Molecular Complexes and Related Systems. . . . . 515
Martin Vacha and Shuzo Hirata
31 Cooperative and Hierarchal Photoresponses of Molecular
Assembling Processes Probed by Organic Fluorescent
Molecules . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 537
Fuyuki Ito
32 Fabrication of Charge-Transfer Complex Nanocrystals Toward
Electric Field-Induced Resistive Switching . . . . . . . . . . . . . . . . . . . 551
Tsunenobu Onodera and Hidetoshi Oikawa
33 Turn-on Mode Photoswitchable Fluorescent Diarylethenes
for Super-Resolution Fluorescence Microscopy. . . . . . . . . . . . . . . . 563
Masakazu Morimoto and Masahiro Irie
34 Crystallization Control of the Photoresponsible Diarylethene
Film with an Aluminum Plasmonic Chip . . . . . . . . . . . . . . . . . . . . 581
Keiko Tawa, Taiga Kadoyama, Ryo Nishimura, and Kingo Uchida