Hydrogen Bonding and Transfer in the Excited State, 2 Volume Set
Initial chapters present both the experimental and theoretical investigations on the excited-state hydrogen bonding structures and dynamics of many organic and biological chromophores. Following this, several chapters describe the influences of the excited-state hydrogen bonding on various photophysical processes and photochemical reactions, for example: hydrogen bonding effects on fluorescence emission behaviors and photoisomerization; the role of hydrogen bonding in photosynthetic water splitting; photoinduced electron transfer and solvation dynamics in room temperature ionic liquids; and hydrogen bonding barrier crossing dynamics at bio-mimicking surfaces. Finally, the book examines experimental and theoretical studies on the nature and control of excited-state hydrogen transfer in various systems.
Hydrogen Bonding and Transfer in the Excited State is an essential overview of this increasingly important field of study, surveying the entire field over 2 volumes, 40 chapters and 1200 pages. It will find a place on the bookshelves of researchers in photochemistry, photobiology, photophysics, physical chemistry and chemical physics.
List of Contributors.
1. Vibrational Dynamics of the Hydrogen Bonds in Nucleic Acid Base Pairs (Yun-An Yan and Oliver Kühn).
1.2 Hydrogen Bonding and Nonlinear Infrared Spectroscopy.
1.3 Correlated Vibrational Dynamics of an Adenine-Uracil Derivative in Solution.
2. Vibrational Energy Relaxation Dynamics of XH Stretching Vibrations of Aromatic Molecules in the Electronic Excited State (Takayuki Ebata).
2.2 IR Spectra of 2-Naphthol and Its H-Bonded Clusters in S1 State.
2.3 VER Dynamics of Bare 2-Naphthol.
2.4 VER Dynamics of H-Bonded Clusters of 2-Naphthol.
2.5 Comparison of the Cis®Trans Barrier Height between S0 and S1.
3. The Hydrogen-Bond Basicity in the Excited State. Concept and Applications (Attila Demeter).
3.3 Result and Discussion.
3.3.1 Absorption and Fluorescence Spectra of the Complexed Species.
3.3.2 Hydrogen-Bond Basicity of the Ground and Singlet Excited State.
3.3.3 Reaction Rate of Hydrogen-Bonded Complex Formation In Excited State.
3.3.4 Solvatochromism of DMAP and Its Singly Complexed Derivative: Estimation of the Dipole Moment of A Singlet Excited Complexes.
3.3.5 Triplet State Properties of the Complexed Species.
4. Solute–Solvent Hydrogen Bond Formation in the Excited State. Experimental and theoretical Evidences (Iulia Matei, Sorana Ionescu, Mihaela Hillebrand).
4.2 The Prerequisite Conditions for Hydrogen Bond Formation.
4.3 Diagnosis Criteria and Quantitative Treatment of the Hydrogen Bonds.
4.4 Design of the Experiments.
4.5 Theoretical Modelling of the H Bonds.
5. Electronic Excited State Structures and Properties of Hydrated Dna Bases and Base Pairs (Manoj K. Shukla and Jerzy Leszczynski).
5.2 Ground State Structures of Nucleic Acid Bases and Base Pairs.
5.3 Excited State Structures of Nucleic Acid Bases.
5.4 Excited States of Base Pairs.
5.5 Excited State Dynamics and Nonradiative Decays.
6. Insight from Singlet into Triplet Excited-State Hydrogen Bonding Dynamics in Solution (Guang-Jiu Zhao and Ke-Li Han).
6.2 Theoretical Methods.
6.3 Results and Discussions.
7. Probing Dynamic Heterogeneity in Nano-Confined Systems: Femtosecond Excitation Wavelength Dependence and FCS (Shantanu Dey, Ujjwal Mandal, Aniruddha Adhikari, Subhadip Ghosh, and Kankan Bhattacharyya).
7.2 Solvation Dynamics in Nano-Confined Systems.
7.3 Fluorescence Resonance Energy Transfer (FRET): lex Dependence.
7.4 Excited State Proton Transfer (ESPT).
7.5 Diffusion of Organic Dyes by Fluorescence Correlation Spectroscopy (FCS).
8. Fluorescence Studies of the Hydrogen Bonding of Excited State Molecules within Supramolecular Host-Guest Inclusion Complexes (Brian D. Wagner).
8.2 Hydrogen Bonding Involving Excited States of Fluorescent Probes in Solution.
8.3 Hydrogen Bonding of Excited States of Included Guests.
9. Hydrogen Bonding on Photoexcitation (Debarati Dey, Manas Kumar Sarangi and Samita Basu).
9.2 Intermolecular Excited State Hydrogen Bonding.
9.3 Concluding Remarks.
10. Effect of Intramolecular H-Bond-Type Interactions on the Photochemistry of Aza-Stilbene-Like Molecules (Giampiero Bartocci, Ugo Mazzucato, and Anna Spalletti).
10.2 IHB Effects on the Photobehaviour of Stilbene-Like Molecules.
11. Hydrogen Bonding Barrier Crossing Dynamics at Bio-Mimicking Surfaces (Rajib Kumar Mitra, Pramod Kumar Verma, Debapriya Banerjee, Samir Kumar Pal).
11.2 Materials and Methods.
11.3 Results and Discussions.
12. Formation of Intermolecular Hydrogen Bonds in the Fluorescence Excited State of Organic Luminophores Containing Simultaneously Carbonyl and Amino Group (Ilijana Timcheva and Peter Nikolov)..
12.3 Results and Discussion.
13. Hydrogen-Bonding Effects on Excited States of Para-Hydroxyphenacyl Compounds (David Lee Phillips).
13.2 Experimental and Computational Methods.
13.3 Hydrogen Bonding Effects on the Excited States of Selected Phenacyl Model Compounds.
13.4 Hydrogen Bonding Effects on the Excited States of Selected Para-Hydroxyphenacyl Ester Phototriggers and the Role of Water in the Deprotection and Subsequent Reactions.
14. Hydrogen Bonding Effects On Intramolecular Charge Transfer (Govindarajan Krishnamoorthy).
14.2 Polarity and Viscosity.
14.3 Hydrogen Bonding with Donor Moiety.
14.4 Hydrogen Bonding with Acceptor Moiety.
15. Chemical Dynamics in Room Temperature Ionic Liquids: the Role of Hydrogen Bonding (Souravi Sarkar, Rajib Pramanik, and Nilmoni Sarkar).
15.1 Photoinduced Electron Transfer in a Room Temperature Ionic Liquid.
15.2 Dynamics of Solvent Relaxation in Room Temperature Ionic Liquids Containing Mixed Solvents.
16. Vibrational Spectroscopy for Studying Hydrogen Bonding in Imidazolium Ionic Liquids and their Mixtures with Co-Solvents (Johannes Kiefer).
16.2 Experimental Approaches.
16.3 Hydrogen Bonding in Ionic Liquids.
16.4 Potential, Challenges and Future Applications.
17. Intramolecular H-Bond Formation Mediated De-Excitation of Curcuminoids: a Time-Resolved Fluorescence Study (Luca Nardo, Alessandra andreoni and Hanne Hjorth Tønnesen).
17.2 Experimental Setup and Data Analysis Methods.
17.3 Results and Discussion.
18. Hydrogen Bonds of Protein-Bound Water Molecules in Rhodopsins (Hideki Kandori).
18.2 Detection of Water Under Strongly Hydrogen-Bonded Conditions in Bacteriorhodopsin.
18.3 Hydration Switch Model as a Proton Transfer Mechanism in the Schiff Base Region of Bacteriorhodopsin.
18.4 Time-Resolved IR Study of Water Structural Changes in Bacteriorhodopsin at Room Temperature.
18.5 Role of Water Hydrogen Bond in Chloride-Ion Pump.
18.6 Strongly Hydrogen-Bonded Water Molecules and Functional Correlation with the Proton-Pump Activity.
19. Ground and Excited State Hydrogen Bonding in the Diazaromatic Betacarboline Derivatives (Carmen Carmona, Manuel Balón, María Asunción Muñoz, Antonio Sánchez-Coronilla, José Hidalgo, and Emilio García-Fernández).
19.2 Hydrogen Bond Interactions Between N9-methyl-9H- pyrido [3,4-b]indole, MBC and N9-methyl-1- methyl- 9H-pyrido[3,4-b]indole, MHN, with 1,1,1,3,3,3- hexafluoro-2-ol, HFIP, in Cyclohexane.
19.3 Hydrogen Bond Interactions between N2-methyl-9H- pyrido[3,4-b]indole, BCA, and HFIP in Cyclohexane.
19.4 Hydrogen Bond Interactions between 9H-pyrido[3,4-b] indole, BC, with HFIP in Cyclohexane.
19.5 Hydrogen Bond Interactions between BC and Pyridine Derivatives in Cyclohexane and in BC Self-Aggregates in 2-methylbutane, 2MB.
19.6 Concluding Remarks.
20. Effect of H-Bonding on the Photophysical Behavior of Coumarin Dyes (Sukhendu Nath, Manoj Kumbhakar, Haridas Pal).
20.2 Effect of Intermolecular H-Bonding.
20.3 Effect of Intramolecular H-Bonding on ICT to TICT Conversion.
21. Role of Hydrogen Bonds in Photosynthetic Water Splitting (Gernot Renger).
21.2 Photosystem II: Overall Reaction Pattern and Cofactor Arrangement.
21.3 Hydrogen Bonds and thermo-Stability of PS II.
21.4 Reaction Sequences of PS II and role of hydrogen bonds.
21.5 Concluding Remarks.
22. Proton Transfer Reactions in the Excited Electronic States (Vladimir I. Tomin).
22.2 ESIPT in 3-Hydroxyflavones and Some Relative Compounds.
22.3 Dynamic Quenching of Fluorescence as a Simple Test for Study of Photochemical Reaction Character.
22.4 Use of Dynamic Quenching of Fluorescence For Study of Reactions From Higher Excited States.
22.5 ESIPT From S2 Singlet State in 3-hydroxyflavone.
22.6 Concluding Remarks.
23. Controlling Excited-State Proton/H-Atom Transfer along Hydrogen-Bonded Wires (Carine Manca Tanner, Christian Tanner, and Samuel Leutwyler).
23.2 Prototype System.
23.3 What Favors/Prevents ESHAT.
24. Excited State Proton Transfer via Hydrogen Bonded Dimers and Complexes in Condensed Phase (Cheng-Chih Hsieh, Chang-Ming Jiang and Pi-Tai Chou).
24.2 Biprotonic transfer within doubly H-bonded homo and heterodimers.
24.3 Proton transfer through host/guest types of hydrogen bonded complexes.
24.4 Solvation dynamics coupled into the proton transfer reaction.
25. QM/MM excited-state molecular dynamics approach using effective fragment potentials method (Tetsuya Taketsugu, Daisuke Kina, Akira Nakayama, Takeshi Noro, and Mark S. Gordon).
25.3 Concluding Remarks.
26. Excited States Intramolecular Proton Transfer Processes on Some Isomeric Naphthalene Derivatives – a DFT Study (Sankar Prasad De and Ajay Misra).
26.2 Theoretical Calculations.
26.3 Results and Discussion.
27. Conformational Switching Between Acids and their Anions by Hydrogen Bonding (Taka-Aki Okamura, Hitoshi Yamamoto, and Norikazu Ueyama).
27.2 pKa Shift of Acids by Neighboring Amide NH.
27.3 Coordination of the Anion Ligand to Metal Ion.
28. Charge Transfer in Excited States: ab initio Molecular Dynamics Simulations (Maciej Koaski, Anupriya Kumar, Han Myoung Lee, Kwang S. Kim).
28.2 Charge-Transfer-to-Solvent-Driven Dissolution Dynamics of I-(H2O)2-5 Upon Excitation.
28.3 Dynamics of Water Photolysis: Excited State and Born-Oppenheimer Molecular Dynamics Study.
28.4 Photo-Dissociation of Hydrated Hydrogen Iodide Clusters: ab initio Molecular Dynamics Simulations.
28.5 Excited State Dynamics of Pyrrole-Water Complexes: ab initio Excited State Molecular Dynamics Simulations.
29. Competitive ESIPT in O-hydroxy Carbonyl Compounds: Perturbation through Solvent Modulation and Internal Torsion (Sivaprasad Mitra).
29.1 Excited State Proton Transfer: an Overview.
29.2 Excited State Intramolecular Proton Transfer (ESIPT).
29.3 ESIPT in O-hydroxy Carbonyl Compounds.
29.4 Concluding Remarks.
30. Excited State Double Hydrogen-Bonding Induced by Charge Transfer in Isomeric Bifunctional Azaaromatic Compounds: Pyrido-Indole and Pyrrolo-Quinoline Derivatives (Dolores Reyman and Cristina Díaz-Oliva).
30.2 Pyrrolo-Quinoline Derivatives (PQ, DPC, TPC).
30.3 Methylene-Bridged 2-(2'-pyridyl)indoles and Pyrido[2,3-a]carbazole (PC).
30.4 Fluorescence Quenching by Electron Transfer in Pyrroloquinolines and Pyin-n.
30.5 Betacarboline Derivatives.
31. Unusual Rheology of Hydrogen Bonded Large Molecular Aggregates of Charged Amphiphiles: Photochemistry and Photophysics of Hydroxy Aromatic Dopants.
31.2 Microstructural Transition of Micelles in Presence of Inorganic and Organic Salts.
31.3 Microstructural Transition of Micelles in Presence of Neutral Aromatic Dopants.
31.4 Photochemistry and Photophysics of Hydroxy Aromatic Compounds.
31.5 Excited State Proton Transfer (ESPT) of Hydroxy Aromatic Compounds.
31.6 ESPT of Hydroxy Aromatic Compounds in Organised Media and Some Unusual Emission Phenomena.
32. Excited-State Intramolecular Proton Transfer in Benzoxazole Derivatives (Yi Pang and Weihua Chen).
32.2 Intromolecular Proton Transfer in 2,5-bis(2’-hydroxy-phenyl)benzoxazole Derivatives.
33. Ultrafast Dynamics of the Excited States of Hydrogen-Bonded Complexes and Solvation (Dipak K. Palit).
33.2 Identification and Characterization of Hydrogen-Bonded Complex.
33.3 Vibrational Dynamics of the C=O Stretching Mode of Fluorenone.
33.4 Dynamics of Excited States of Hydrogen-Bonded Complex.
33.5 Summary and Conclusion.
34. Reaction Volume for the Photoinduced Proton Transfer in Aqueous Solutions of 6-methoxyquinoline (Stefania Abbruzzetti and Cristiano Viappiani).
34.2 Materials and Methods.
34.3 Results and Discussion.
35. Molecular Recognition and Chemical Sensing of Anions Utilizing Excited-State Hydrogen-Bonding Interaction (Ashutosh S. Singh and Shih-Sheng Sun).
35.1 Recognition and Sensing of Anions by Intramolecular Hydrogen Bonding in Excited States.
35.2 Recognition and Sensing of Anions by Intermolecular Hydrogen Bonding in Excited States.
35.3 Recognition and Sensing of Anions by Conjugated Polymers through ESIPT.
36. Theoretical Studies of Green and Red Fluorescent Proteins (Hong Zhang, Qiao Sun, Sufan Wang, Seth Olsen, Sean C. Smith).
36.2 Method of Calculation.
36.3 Results and Discussion.
36.4 Conclusions & Future Work.
37. Changes in Active Site Hydrogen Bonding upon the Formation of the Electronically Excited State of Photoactive Yellow Protein (Wouter D. Hoff, Zhouyang Kang, Masato Kumauchi, Aihua Xie).
37.1 Central Importance of Light in Biology.
37.2 Possible Importance of Excited State Hydrogen Bonding in Photoreceptors.
37.3 Introduction To Photoactive Yellow Protein.
37.4 Hydrogen Bonding in the Initial State of PYP.
37.5 Assignment of Vibrational Modes in PYP.
37.6 Identification of Vibrational Structural Markers.
37.7 Changes In Hydrogen Bonding During the Initial Stages of the PYP Photocycle.
37.8 Sub-Picosecond Time Resolved Transient Spectroscopy of PYP.
37.9 Changes in Active Site Hydrogen Bonding Upon the Formation of the S1 State of PYP.
38. Ultrafast Catalytic Processes in the Light-Driven Enzyme Protochlorophyllide Oxidoreductase (POR) (Marie Louise Groot and Derren James Heyes).
38.2 Protochlorophyllide Oxidoreductase (POR).
38.3 The Catalytic Mechanism of POR.
38.4 Ultrafast Catalytic Processes of the Isolated Pchlide Species.
38.5 Ultrafast Catalytic Processes of the Enzyme-Bound Pchlide Species.
39. Photodissociation of Molecules in Hydrogen Bonded Clusters Probing the Excited State (Michal Fárník, Petr Slavíek and Udo Buck).
39.3 Aqueous Photochemistry From the Cluster Perspective.
39.4 Hydrogen Bonded Clusters of Nitrogen Heterocycles.
39.5 General Conclusions and Outlook.
Guang-Jiu Zhao, State Key Laboratory of Molecular Reaction Dynamics, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian, China.