Infrared-optical double-resonance measurements of hydrogen-bonding interactions in clusters involving aminophthalimides

Abstract We have used infrared spectroscopy in both the ground and excited electronic states to determine the structural geometries of hydrogen-bonded clusters involving aminophthalimide molecules. This provides a higher level of structural information than available through an inertial measurement such as rotational coherence spectroscopy. Clusters of interest include the two conformers each of the water n=1 cluster with 4-aminophthalimide (4AP) and 4-amino-N-methylphthalimide (4ANMP), which are shown to be attached by proton donation to different >CO groups. The corresponding n=1 water cluster of 3-aminophthalimide (3AP) is present as only a single conformer, consistently with the presence of an intramolecular hydrogen bond. Both 3AP/(H2O)1 and 4AP/(H2O)1 are found to form bridging structures between the imide N–H bond and an adjacent >CO group. On the other hand, the water dimer clusters of 4AP and 4ANMP bridge the NH2 and the adjacent >CO group. Pure dimers of the aminophthalimides have simple infrared spectra in the electronic ground states, which indicate symmetrical structures. The 4AP and 4ANMP dimers form a double hydrogen-bonded bridge across the 2,4 positions and their complex infrared spectra in the excited state show evidence of strong interactions, which may involve excited-state intermolecular double proton transfer. On the other hand, the 3AP dimer is doubly hydrogen bonded across the 1,7 positions, and appears to show evidence of excited-state single intramolecular proton transfer. Possible reasons for these differences are discussed.

[1]  G. Gurzadyan,et al.  Femtosecond Spectroscopic Study of Relaxation Processes of Three Amino-Substituted Coumarin Dyes in Methanol and Dimethyl Sulfoxide , 1998 .

[2]  Eyal Nir,et al.  Pairing of isolated nucleic-acid bases in the absence of the DNA backbone , 2022 .

[3]  M. R. Topp,et al.  Conformational barrier crossing in the water dimer cluster of coumarin 151 studied by infrared optical double-resonance spectroscopy , 2001 .

[4]  C. Carter,et al.  High-Resolution Laser-Induced Fluorescence Spectra of 7-Azaindole−Water Complexes and 7-Azaindole Dimer , 1997 .

[5]  T. Zwier,et al.  Resonant ion-dip infrared spectroscopy of benzene–(water)n–(methanol)m clusters with n+m=4, 5 , 1998 .

[6]  K. Fuke,et al.  Electronic spectra and tautomerism of hydrogen-bonded complexes of 7-azaindole in a supersonic jet , 1984 .

[7]  T. Ebata,et al.  Vibrational spectroscopy of 2-pyridone and its clusters in supersonic jets: Structures of the clusters as revealed by characteristic shifts of the NH and C=O bands , 1999 .

[8]  S. Leutwyler,et al.  Intermolecular vibrations of jet-cooled (2-pyridone) 2 : A model for the uracil dimer , 2000 .

[9]  T. Zwier,et al.  The hydrogen-bonding topologies of indole–(water)n clusters from resonant ion-dip infrared spectroscopy , 1998 .

[10]  E. Laitinen,et al.  Solvation dynamics study of 3-aminophthalimide in n-butanol solution at different temperatures , 1996 .

[11]  L. Grace,et al.  REMPI Spectroscopy of Jet-Cooled Guanine , 1999 .

[12]  Peter P. Chow,et al.  Nanosecond Time-Resolved Emission Spectroscopy: Spectral Shifts due to Solvent-Excited Solute Relaxation , 1971 .

[13]  Eyal Nir,et al.  Guanine tautomerism revealed by UV–UV and IR–UV hole burning spectroscopy , 2001 .

[14]  Guilford Jones,et al.  Solvent effects on emission yield and lifetime for coumarin laser dyes. Requirements for a rotatory decay mechanism , 1983 .

[15]  J. Simons,et al.  IR−UV Ion-Dip Spectroscopy ofN-Benzylformamide Clusters: Stepwise Hydration of a Model Peptide , 2000 .

[16]  E. Laitinen,et al.  Solvation dynamics study of 4‐amino‐N‐methyl‐phthalimide in n‐alcohol solutions , 1996 .

[17]  S. Saha,et al.  The Fluorescence Response of a Structurally Modified 4-Aminophthalimide Derivative Covalently Attached to a Fatty Acid in Homogeneous and Micellar Environments , 1999 .

[18]  J. Simons,et al.  IR-UV ion-depletion and fluorescence spectroscopy of 2-phenylacetamide clusters : hydration of a primary amide , 2001 .

[19]  P. Barbara,et al.  Time-resolved spectroscopic measurements on microscopic solvation dynamics , 1987 .

[20]  Z. Huang,et al.  High‐resolution near‐infrared spectroscopy of water dimer , 1989 .

[21]  E. Bernstein,et al.  7-Azaindole and its clusters with argon, methane, water, ammonia, and alcohols: molecular geometry, cluster geometry, and nature of the first excited singlet electronic state , 1990 .

[22]  Yuhui Huang,et al.  Spectroscopy and Fluorescence Lifetimes of Jet-Cooled 7-Azaindole: Electronic States and Solvent Complex Geometry , 1996 .

[23]  K. Fuke,et al.  Double-proton-transfer reaction in the excited state of 1-azacarbazole dimer and 1-azacarbazole-7-azaindole heterodimer studied in a supersonic jet , 1986 .

[24]  M. R. Topp,et al.  Simple water clusters of Coumarins 151 and 152A studied by IR–UV double resonance spectroscopy , 2000 .

[25]  R. Micheels,et al.  Picosecond dynamics of double proton transfer in 7-azaindole dimers , 1979 .

[26]  R. W. Fessenden,et al.  Role of Nonfluorescent Twisted Intramolecular Charge Transfer State on the Photophysical Behavior of Aminophthalimide Dyes , 1996 .

[27]  P. Suppan,et al.  Photophysics of aminophthalimides in solution. I, Steady-state spectroscopy , 1991 .

[28]  K. Fuke,et al.  Dynamics of double-proton-transfer reaction in the excited-state model hydrogen-bonded base pairs , 1989 .

[29]  M. Maroncelli,et al.  Polar solvation dynamics of polyatomic solutes: Simulation studies in acetonitrile and methanol , 1995 .

[30]  H. Murakami.  Femtosecond time-resolved fluorescence spectra of a coumarin dye in glycerol , 2000 .

[31]  M. Maroncelli,et al.  Estimating the time-zero spectrum in time-resolved emmsion measurements of solvation dynamics , 1994 .

[32]  G. Köhler,et al.  Excited state properties and deactivation pathways of 7-aminocoumarins , 1994 .

[33]  A. Iwasaki,et al.  Infrared Spectroscopy of Hydrogen-Bonded Phenol−Amine Clusters in Supersonic Jets , 1996 .

[34]  A. H. Huizer,et al.  Non-exponential solvation dynamics of electronically excited 4-aminophthalimide in n-alcohols , 1995 .

[35]  A. Zewail,et al.  Femtosecond Dynamics of a Hydrogen-Bonded Model Base Pair in the Condensed Phase: Double Proton Transfer in 7-Azaindole , 1998 .

[36]  A. Bach,et al.  Water–wire clusters: Vibronic spectra of 7-hydroxyquinoline⋅(H2O)3 , 2000 .

[37]  M. Maroncelli,et al.  Rotational Dynamics of Coumarin 153: Time-Dependent Friction, Dielectric Friction, and Other Nonhydrodynamic Effects , 1997 .

[38]  S. Kovalenko,et al.  Ultrafast strokes shift and excited-state transient absorption of coumarin 153 in solution , 1997 .

[39]  M. Kasha,et al.  Excited-state two-proton tautomerism in hydrogen-bonded n-heterocyclic base pairs. , 1969, Proceedings of the National Academy of Sciences of the United States of America.

[40]  J. Miyawaki,et al.  Infrared Depletion Spectroscopy of the Aniline Dimer , 1996 .

[41]  A. Castleman,et al.  Femtosecond cluster studies of the solvated 7-azaindole excited state double-proton transfer. , 1999, Proceedings of the National Academy of Sciences of the United States of America.

[42]  M. R. Topp,et al.  Excited state interactions in the doubly hydrogen-bonded jet-cooled dimers of 4-aminophthalimide and 4-amino-N-methylphthalimide , 2002 .

[43]  A. H. Zewail,et al.  Femtosecond molecular dynamics of tautomerization in model base pairs , 1995, Nature.

[44]  K. Weisz,et al.  Novel phthalimide nucleosides for the specific recognition of a CG Watson–Crick base pair , 2001 .

[45]  Tarasankar Pal,et al.  Molecular Photonic Switches Employing Ions and Nanoparticles of Coinage and Platinum Metals , 2000 .

[46]  A. Zewail,et al.  Femtosecond Dynamics of Double Proton Transfer in a Model DNA Base Pair: 7-Azaindole Dimers in the Condensed Phase , 1999 .

[47]  T. Zwier,et al.  Probing hydrogen bonding in benzene–(water)n clusters using resonant ion–dip IR spectroscopy , 1994 .

[48]  O. A. Seoud,et al.  Solvatochromism in Cationic Micellar Solutions: Effects of the Molecular Structures of the Solvatochromic Probe and the Surfactant Headgroup , 2001 .

[49]  J. S. D. Melo,et al.  Spectroscopy and photophysics of 4- and 7-hydroxycoumarins and their thione analogs , 2001 .

[50]  A. Castleman,et al.  Excited state double proton transfer in the 7-azaindole dimer revisited , 2000 .

[51]  M. R. Topp,et al.  Spectroscopy of jet-cooled water complexes with coumarin 151: Observation of vibronically induced conformational barrier crossing , 1998 .

[52]  D. Huppert,et al.  Excited State Proton-Transfer Reactions of Coumarin 4 in Protic Solvents , 2001 .

[53]  T. Troxler,et al.  Spectroscopy of jet-cooled polar complexes of aminophthalimides , 1997 .

[54]  M. Viant,et al.  Infrared laser spectroscopy of uracil in a pulsed slit jet , 1995 .

[55]  M. Maroncelli,et al.  Picosecond solvation dynamics of coumarin 153: The importance of molecular aspects of solvation , 1987 .