Toward molecular switches and biochemical detectors employing adaptive femtosecond-scale laser pulses

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Toward molecular switches and biochemical detectors employing adaptive femtosecond-scale laser pulses Petra Sauer and Roland E. Allen, Institute for Quantum Studies and Physics Department, Texas A&M University Cis to trans (and trans to cis) photoisomerization of azobenzene, with nuclear motion allowing extra electronic transitions for pulse durations > about 50 fs UV or visible UV or visible Photoinduced ring-opening (and ring-closing) in a model dithienylethene visible UV! Response of dipicolinic acid to femtosecond-scale laser pulses, including excited states and nuclear motion (with Yuri Rostovtsev)

Representative applications: azobenzene Holographic data storage Light-driven molecular switch Photoelectrochemical Storage Liquid Crystal Display Instigator for Protein Folding Nanomechanical Device Droplet Driver Control of Protein Activity 2

One major result from these simulations -- we find that photochemical reactions involve: multiple steps (e.g., first S 0 S 1, and subsequently S 0 S 2 because nuclei move, or first S 2 S 1 and then S 1 S 0 for later de-excitation of the molecule) multiple excitations (e.g., linear combination of S 0, S 1, S 2, S 3 ) multiple configuration coordinates (e.g., rotational dihedral angle and length of central bond) In the present picture, with configuration interaction neglected, S 0 is the ground state S 1 is the excitation of one electron from HOMO to LUMO (highest occupied molecular orbital to lowest unoccupied molecular orbital) S 2 is the excitation of one electron from HOMO-1 to LUMO (from next-to-highest occupied molecular orbital) S 3 is the excitation of two electrons from HOMO to LUMO 3

We call our technique semiclassical electron-radiation-ion dynamics (SERID) to emphasize the limiting approximations: The radiation field and nuclear motion are both treated classically, and the ion cores are regarded as inert (with only the valence electrons included in the dynamics). Recall, however, that one still observes n-photon and n-phonon processes in a semiclassical treatment. Also, the nuclear motion is treated correctly on reasonably short time scales (e.g., picoseconds). List of approximations in present calculations: 1. The atomic nuclei are treated as positive point charges. 2. The treatment is nonrelativistic. 3. The nuclear motion is treated classically. 4. The radiation field is treated classically. 5. The electrons are treated in a time-dependent mean-field picture, with many-body effects neglected. 6. Only the valence electrons are treated, with the inner electrons plus nucleus represented as an inert core. 7. The basis functions are atomic orbitals. 8. The spin-orbit interaction, exchange interaction, and other spin-dependent interactions are neglected. 9. The calculations are not explicitly self-consistent,and there is no explicit Coulomb repulsion. 10. The Hamiltonian matrix elements and core-core repulsion are determined from density-functional calculations involving pairs of atoms. 11. The Peierls substitution is used to couple the electrons to the radiation field. 4 12. The influence of a larger environment is not included.

Density-functional-based parameterization of the electronic Hamiltonian H and the effective repulsive potential U: D. Porezag, Th. Frauenheim, et al., Phys. Rev B 51, 12947 (1991) P. Sauer and R. E. Allen, J. Mod. Optics 53, 2619 (2006) 5

6

Ehrenfest's theorem states that M d 2 X! dt 2 =! "H "X! where X! is the operator corresponding to any nuclear coordinate, M is the corresponding mass, and H is the full Hamiltonian for all particles in the molecule. If the electrons are treated in a time-dependent self-consistent field picture, and the one-electron wavefunctions are represented in terms of localized basis functions, one obtains M d 2 X! =! "# $H $#" % t " dt 2 j ( t ( ) )# $X! #" "# ( j t )! $U rep $X!. j Since quantum fluctuations, in the present context, are typically smaller than 0.05 Å for C and smaller than 0.10 Å even for H, it is a reasonable approximation to expand in a Taylor series about the expectation value:!x $ =!H!"# " t $ #!X $!H!"# ( t) ( ) % ' +!H!"# " t $ &!X $ X $ = X $ # ( ) ( ) ) + O ( X $ ( X $ ) 2 + % ' X $ ( X $ & X $ = X $ With X! X!, and with terms that are second-order in the quantum fluctuations neglected, we then take the expectation value to obtain the equation used for the nuclear motion: ( ) M d 2 X =!!" $H #"! % t " dt 2 j ( t)# $X #"!" j t j * ( )! $U rep $X., -.. 7

photoisomerization of azobenzene ΔΕ cis to trans ~ 0.50 ev cis E(TS) ~ 1.00 ev C 2!! trans C 2h UV or visible UV or visible 8

What is already known about the isomerization process: Schematic of electronic energy levels for cis and trans forms S 2 S 1 n!! *!!! * S 0 Photoisomerization quantum yields for S 1 >> than for S 2 [P. Bortolus and S. Monti, J. Phys. Chem. 83, 648 (1979)]. Dominant isomerization product from cis state forms within 170 fs, and from trans state within 320 fs [T. Naegele et al., Chem. Phys. Lett. 272, 489 (1997)]. First configuration interaction calculations indicated an inversion pathway for S 1 excitation (which involves opening a CNN bond angle, with planar motion) and a rotation pathway for S 2 excitation (which involves rotation through the central CNNC dihedral angle) [S. Monti et al, Chem. Phys. 71, 87 (1982)]. Later calculations suggest that rotation pathway is most probable mechanism for both [T. Ishikawa et al, J. Chem Phys. 115, 9 7503 (2001)].

SERID calculated molecular orbital structure CIS LUMO HOMO HOMO-1 LUMO TRANS HOMO-1 HOMO 10

SERID results for S 1 excitation: electron dynamics during excitation Prepare state with an ultrashort 10 fs (FWHM) pulse, so that ion core motion during excitation is minimal, and transition is thus predominantly HOMO to LUMO. molecular orbital population molecular orbital energy laser pulse duration (FWHM) = 10 fs, photon energy = 3.55 ev, fluence = 0.28 kj/m 2, T = 0 K 11

Electron dynamics following HOMO to LUMO excitation molecular orbital population molecular orbital energy 75 fs Between ~ 50 and 100 fs, a series of avoided crossings leads to the transfer of ~ 0.6 electrons downward from LUMO to HOMO. 12

SERID results for S 1 excitation: nuclear dynamics The SERID simulations indicate rotational pathway rather than inversion pathway for S 1 excitation. 13

SERID results for S 2 excitation: electron dynamics during excitation Prepare excited state with an ultrashort 10 fs (FWHM) pulse, so that nuclear motion during excitation is minimal, and transition is predominantly HOMO-1 to LUMO. molecular orbital population molecular orbital energy laser pulse duration (FWHM) = 10 fs, photon energy = 4.18 ev, fluence = 0.15 kj/m 2, T = 0 K 14

Electron dynamics following HOMO-1 to LUMO excitation molecular orbital population molecular orbital energy 780 fs 900 fs At about 780 fs, a HOMO-1/HOMO avoided crossing leads to a transfer of roughly 0.60 holes up from the HOMO-1 into the HOMO. A subsequent HOMO/LUMO avoided crossing at about 900 fs then 15 transfers ~ 0.7 electrons down from the LUMO into the HOMO.

SERID results for S 2 excitation: nuclear dynamics The SERID simulations indicate rotational mechanism for S 2 excitation, occurring in the excited state, followed by return to the ground state. 16

Excitation with 100 fs (FWHM) pulse: electron dynamics during excitation Longer pulse initially excites electrons from HOMO to LUMO. As nuclei move, electrons are excited from HOMO-1 to LUMO. molecular orbital population molecular orbital energy laser pulse duration (FWHM) = 100 fs, photon energy = 3.55 ev, fluence = 0.47 kj/m 2, T = 0K 17

Excitation with 100 fs (FWHM) pulse: nuclear dynamics during excitation 18

Excitation with 100 fs (FWHM) pulse: electron dynamics after excitation molecular orbital population molecular orbital energy 260 fs 340 fs At about 260 fs, an avoided crossing between HOMO-1 and HOMO leads to a transfer of roughly 0.70 holes up into the HOMO. A subsequent series of HOMO-LUMO avoided crossings, between 340 fs and 550 fs, transfer ~ 0.3 electrons down into the HOMO. 19

Excitation with 100 fs (FWHM) pulse: nuclear dynamics after excitation Depopulation of the excited states occurs as the isomerization proceeds along a rotational pathway. 20

Summary for azobenzene isomerization An ultrashort 10 fs (FWHM) pulse matched to the HOMO-LUMO energy gap excites electrons from HOMO to LUMO. Isomerization proceeds along a rotational pathway. An avoided crossing between HOMO and LUMO, approximately halfway between cis and trans geometries, transfers the electronic population back into the ground state. An ultrashort 10 fs (FWHM) pulse, matched to the HOMO-1 to LUMO energy gap, excites electrons predominantly from HOMO-1 to LUMO. Isomerization again proceeds along a rotational pathway. An avoided crossing between HOMO-1 and HOMO near the trans configuration transfers hole population from HOMO-1 to HOMO. A later avoided crossing between HOMO and LUMO transfers electrons to the HOMO. A longer 100 fs (FWHM) laser pulse matched to the HOMO-LUMO energy gap excites electrons from both HOMO-1 and HOMO into the LUMO. The second excitation is due to nuclear motion during pulse excitation. An avoided crossing between HOMO-1 and HOMO near the cis configuration transfers hole population from HOMO-1 to HOMO. A subsequent HOMO-LUMO avoided crossing halfway between cis and trans configurations transfers electron population back into the ground state. 21

Lower fluence no isomerization: electron dynamics population during excitation molecular orbital energy during excitation population after excitation molecular orbital energy after excitation No HOMO-1/HOMO avoided crossing => no transfer of holes from HOMO-1 to HOMO. Then high occupancy of HOMO => no transfer of electrons from 22 LUMO to HOMO, despite HOMO/LUMO avoided crossings.

Lower fluence no isomerization: nuclear dynamics C a -N-N-C a during excitation C b -C a -N-N during excitation C a -N-N-C a after excitation C b -C a -N-N after excitation Similar behavior as with more intense laser pulse, except amplitude of oscillations not as large. Molecule never reaches geometry 23 required for HOMO-1/HOMO avoided crossing.

dithienylethene model system Both forms have C 2 symmetry. closed open barrier height much larger than openclosed energy difference visible UV 24

SERID calculated molecular orbital structure CLOSED ΔΕ g =1.53 ev HOMO LUMO OPEN ΔΕ g =3.14 ev HOMO LUMO 25

Electron dynamics during excitation Initial excitation is from HOMO into LUMO. Nuclear motion subsequently permits additional excitations out of HOMO-1 and into LUMO+1. orbital population orbital energy pulse duration (FWHM) = 150 fs,!! = 1.8 ev, F = 0.44 kj/m 2, T = 300 K 26

Nuclear dynamics during excitation C c -C c bond length C b -C a -C a -C b angle C a -C a bond length C c -C C c bondlength a -C b bond length 27

Electron dynamics leading to bond breakage Orbital Population Orbital Energy At ~ 785 fs: electron transfer from LUMO+1 to LUMO At ~ 960 fs: hole transfer from HOMO-1 to HOMO and electron transfer from LUMO+1 to LUMO 28

Electron dynamics following bond breakage orbital population orbital energy Between ~ 1 ps and 4 ps, a series of avoided crossings between HOMO and LUMO return molecule to the ground state. 29

Nuclear dynamics following excitation C c -C c bond length C b -C a -C a -C b angle Bond breaks at ~ 1 ps Ring opening, followed by rotation about central dihedral angle, until molecule returns to ground state at ~ 4 ps. 30

Nuclear dynamics following excitation (continued) C a -C a bond length C a -C b bond length tendency toward double bond after final HOMO-LUMO exchange of electron occupancy tendency toward single bond after final HOMO-LUMO exchange 31

Summary of ring-opening mechanism Laser pulse, matched to the HOMO-LUMO energy difference, initially excites electrons from HOMO to LUMO. Nuclear motion subsequently permits excitations out of HOMO-1 and into LUMO+1. After laser pulse excitation, an avoided crossing between HOMO-1 and HOMO transfers holes into the HOMO. An avoided crossing between LUMO+1 and LUMO transfers electrons into LUMO. Following these population transfers, ring-opening occurs at ~ 1 ps. A series of HOMO-LUMO avoided crossings, which occur between ~ 1ps and 4 ps, transfer electronic population back to the ground state. 32

dipicolinic acid (DPA): electronic and vibrational response 33

Bacterial Spore Cortex Coat Core S. Kozuka, Y. Yasud and K. Tochikubo, J. Bacteriol. 162, 1250 (1985) Between ~ 5 % and 15 % of dry spore weight (in compounds) 34

Overview of the parameterization scheme for nitrogen and oxygen We scale the density-functional-based hydrogen and carbon pairwise interactions to include interactions with nitrogen and oxygen. I. Electronic Properties II. Parameterization scheme consists of two parts: Diagonal Hamiltonian matrix elements (H ii ) scaled to the s and p atomic energies of the new atom Diagonal elements of the overlap matrix (S ii ) unchanged (equal to 1) Off-diagonal elements of the Hamiltonian scaled so that the energy eigenvalue difference of the active space region equals the energy difference calculated using DFT. The off-diagonal elements of the overlap matrix are left unchanged. Structural Properties The repulsive potential is scaled to match the structural properties (i.e. bond lengths and vibrational frequencies) of the diatomic molecule corresponding to a given pairwise interaction. 35

Parameterization scheme: electronic properties Schematic illustration for parameterizing nitrogen-nitrogen interactions starting with carbon-carbon interactions: C 2 (N 2 ) H ij = i H j and S ij = i j eigenvalues of!"# #" $ #" H!" = # S!" 36

Parameterization scheme: structural properties We then scale the effective nuclear repulsive potential: V new (r new ) = (c 0 + c 1 r)v old (r old ). The constants c 0 and c 1 are determined from the equilibrium conditions ( de rep dr + de elec dr ) r =r 0 = 0 ( d 2 E rep and dr 2 + d 2 E elec dr 2 ) r =r0 = M! 2 where the derivatives of the electronic energy are determined numerically from the scaled Hamiltonian and the overlap matrix:!e elec!x = % " n (!H!x # $!S n!x )" f (n) n n - /! 2 E elec = 2 /!x 2 / /./, n % ' ' ' ' & 2 %!H " n!x # $!S ( ( n & '!x ) * ", m * $ n # $ f (n) * m * * ) m+n,$m +$ n %! 2 H + " n!x # 2!$ n, & ' 2!x n!s!x # $ n 0 2! 2 S (!x 2 ) * " f (n) 2 n 2 2 12 37.

Results of the parameterization for various diatomics Molecule Scale Factor Property Exp. SERID Molecule Scale Factor Property Exp. SERID N 2 CN O 2 CO NO 1.38 1.13 0.67 1.38 0.62 r o (Å) ω (cm -1 ) D 0 (ev) ΔE g (ev) r o (Å) ω (cm -1 ) D 0 (ev) ΔE g (ev) r o (Å) ω (cm -1 ) D 0 (ev) ΔE g (ev) r o (Å) ω (cm -1 ) D 0 (ev) ΔE g (ev) r o (Å) ω (cm -1 ) D 0 (ev) ΔE g (ev) 1.0977 2358.57 9.76 9.30 1.1718 2068.59 7.60 8.25 1.2075 1580.19 5.08 8.61 1.1282 2169.81 11.11 8.39 1.1508 1904.20 6.50 5.63 1.0982 2352.54 19.29 9.68 1.1724 2062.18 10.34 7.54 1.2082 1576.93 6.62 5.77 1.1287 2163.61 12.83 8.69 1.1515 1897.28 4.71 5.74 NH OH 0.81 0.94 r o (Å) ω (cm -1 ) D 0 (ev) ΔE g (ev) r o (Å) ω (cm -1 ) D 0 (ev) ΔE g (ev) 1.0378 3282.30 3.80 8.25 0.9705 3737.76 4.35 7.09 1.0403 3240.56 3.48 8.21 0.9724 3705.94 3.57 10.54 In all cases the experimental bond lengths and frequencies were taken from the CRC Handbook of Chem. and Phys. (2004) online, the binding energies from Herzberg, Spectra of Diatomic Molecules (1989) and the excitation energies from a B3LYP//augccpVQZ calculation, except for the hydride bond lengths, which were taken from Sun et al, J. Chem Phys. 74, 6842 (1981), and the excitation energy of N2, which was calculated without diffuse functions. 38

Parameterization applied to the equilibrium states of the azabenzenes Molecule Bond Exp. (Å) SERID (Å) pyrazine 1 C-C C-N C-H 1.397 1.338 1.083 1.394 1.359 1.087 pyrazine pyridine pyridazine pyrimidine pyridazine 2 pyridine 2 pyrimidine 1 N-N N-C a C a -C b C b -C b C a -H C b -H N-C a C a -C b C b -C c C a -H a C b -H b C c -H c C a -N C a -N C b -C c C a -H a C b -H b C c -H c 1.337 1.338 1.400 1.385 1.079 1.071 1.340 1.395 1.394 1.084 1.081 1.077 1.328 1.350 1.393 1.082 1.079 1.087 1.336 1.362 1.393 1.395 1.092 1.097 1.361 1.396 1.398 1.090 1.097 1.097 1.353 1.362 1.392 1.082 1.090 1.096 1 Cradoc et. al., J. Am. Chem. Soc. (1988). 2 Hannay et. al., J. Chem. Phys. (1999). 3 Haettig et. al., J. Chem. Phys. (1998). 4 Osamura et. al., J. Am. Chem. Soc. (1987). tetrazine 3 C-N N-N C-H 1.341 1.326 1.073 1.359 1.342 1.082 tetrazine s-triazine triazine 4 C-N C-H 1.338 1.084 1.358 1.084 39

Parameterization applied to the equilibrium states of various oxygen-containing molecules Molecule Bond SERID (Å) Exp. (Å) CO 2 1 C-O 1.177 1.162 acetaldehyde acetone acetic acid ethanol H 2 O 1 Acetaldehyde 1 Acetic Acid 2 Furan 1 Acetone 1 O-H C a -O C a -C b C a -H C b -H C-C C-O a C-O b C-H O b -H C b -C b C a -C b C a -O C-H C-C C-O C-H 0.979 1.208 1.520 1.146 1.097 1.531 1.251 1.361 1.099 0.965 1.432 1.391 1.363 1.088 1.534 1.236 1.097 0.957 1.216 1.501 1.114 1.086 1.520 1.214 1.364 1.100 0.971 1.431 1.361 1.362 1.076 1.515 1.215 1.086 1 CRC Handbook of Chem. and Physics (2004) online. 2 Herzberg, Spectra of Diatomic Molecules (1989) furan Ethanol 2 C a -C b O-H C a -O C a -H C b -H 1.537 0.961 1.415 1.113 1.096 1.512 0.971 1.431 1.100 1.090 40

Summary of Parameterization Scheme Hamiltonian and overlap matrix elements scaled to the electronic properties for the relevant pairwise interaction. Effective nuclear repulsion then scaled to the equilibrium bond lengths and vibrational frequencies of the diatomic molecule corresponding to the desired pairwise interaction. Parameterization scheme yields bond lengths for larger molecules that are normally within 2-3% of the experimental bond lengths (and within 5% in every case). 41

Equilibration Method for DPA y Equilibration of the Total Energy x Equilibration of the C a -C b Bonds We obtained the equilibrium configuration of DPA through a 2000 fs simulation in which the velocity of each atom was reduced by 0.3% at each time step. 42

Nuclear equilibrium properties Bond Bond lengths SERID (Å) MCSCF/ 6-21G (Å) * N-C a 1.378 1.338 C a -C b 1.401 1.398 C b -C c 1.394 1.395 C a -C d 1.509 1.484 C d -O a 1.260 1.216 C d -O b 1.327 1.336 H a -O b 0.948 0.955 H b -C b 1.096 1.070 H c -C c 1.096 1.071 Key Normal Modes Excited During Laser Pulse Simulation Description Ring stretch Ring breathe Ring breathe Ring shear Ring stretch SERID (cm -1 ) 702 1070 1270 1671 1738 B3LYP/ cc-pvdz (cm -1 ) 640 1012 1241 1625 1632 * Hameka et al. J. Mol. Structure, 365 (1996) 131. 43

Electronic equilibrium properties Level SERID (ev) B3LYP/ cc-pvdz (ev) HOMO-3-7.79-8.42 HOMO-2-7.20-7.77 HOMO-1-7.05-7.75 HOMO -6.89-7.35 SERID: LUMO -2.86-2.01 ΔE gap = 4.03 ev HOMO-2, HOMO-1, and HOMO nearly degenerate LUMO+1 LUMO+2-2.59-0.35-1.89 +0.37 LUMO and LUMO+1 nearly degenerate LUMO+3 +0.99 +1.33 44

DPA subjected to a (010) polarized pulse matched to the HOMO-2 to LUMO+1 transition frequency Applied Pulse Shape: Laser Pulse Parameters: t pulse (FWHM) = 5 fs A 0 = 0.13 G cm E = 4.61 ev (010) polarization #!(t) =! " cos! $ %!(t " tpulse / 2) & ' ( sin()t) tpulse 45

Normalized frequency spectrum after completion of laser pulse 1036 cm -1 The two peaks with the largest intensity correspond to two ring breathing modes. 1270 cm -1 46

Absorption spectrum Experiment B3LYP/6-311G+(2df,2pd) ~ 270 nm R. Nudelman, B. V. Bronk, and S. Ferima, Appl. Spect. 54 (2000) 445. DFT calculation after J. R. Xie, V. H. Smith, and R. E. Allen, Chem. Phys. (2005). 47

Molecular orbitals involved in transitions π to π* at 231 nm (y-dipole) π to π* at 246 nm (x-dipole) Artificially broadened spectrum: n f i # i! (" ) = & " $ % i i=1 ( ) 2 $ # i 2 f i = oscillator strength Ω i = transition frequency Γ i = half-width of transition n all transitions from filled to unfilled orbitals z n to π* at 298 nm y 48 x

SERID calculated transitions Choose short pulse in order to excite a wide possible range of transitions. E = 4.03 ev t pulse (FWHM)=5 fs polarization is (100) T = 0 K transition from HOMO-2 to LUMO (E = 4.34 ev, λ = 286 nm) E = 4.03 ev t pulse (FWHM)=5 fs polarization is (010) T = 0 K transition from HOMO-2 to LUMO+1 (E = 4.61 ev, λ = 269 nm) 49

SERID excitation spectrum with frozen nuclei (1 0 0) (0 1 0) ( ) = 1.130e #! " $!" # 4.339 ev' % & 0.028 ev ( ) 2 ( ) = 1.020 e #! " $!" # 4.613eV' % & 0.028 ev ( ) 2 A t ( )! cos I t # % $ # % $! 2t pulse ( )! cos 2! 2t pulse # $ % t " t pulse 2 # $ % t " t pulse 2 & & ' ( ( ' & & ' ( ( '!t ~ t pulse = 25 fs 4!E!t! "!E! 0.026eV 50

SERID calculated excitation spectrum with nuclear motion at 0 K fluence = 1.80 10-3 kj/m 2 and (1 0 0) polarization! (" ) = 0.383 e # $!" # 4.289 ev' % & 0.033eV ( ) 2 Average Transition Energy As absorption increases, the transition energy decreases, causing shift to lower frequencies plateau region for higher frequencies abrupt cut-off for lower frequencies 51

SERID calculated excitation spectrum about 4.34 ev with T = 300 K fluence = 1.80 10-3 kj/m 2 and (1 0 0) polarization Low energy sidebands due to excitation out of HOMO-1 and HOMO orbitals High energy sidebands due to excitations to LUMO+1 orbital.! (" ) = 0.323e # $!" # 4.301eV' % & 0.095 ev ( ) 2 52

Comparison of excitation spectra Nuclear motion decreases, shifts, and broadens the absorption spectra. 53

SERID calculated excitation spectrum about 4.61 ev with T = 300 K fluence = 1.80 10-3 kj/m 2 and (0 1 0) polarization Steady increase in absorption with increasing frequency, due to excitations from orbitals below HOMO-2.! (" ) = 0.195 e # $!" # 4.645eV' % & 0.266 ev ( ) 2 54

Full SERID calculated excitation spectrum 288 nm 270 nm R. Nudelman, B. V. Bronk and S. Ferima, Appl. Spect. 54, 445 (2000). Gaussian fit (sum of x- and y- polarized fits):! (") = 0.10 e $ " # 270.1nm ' # % & 10.29 nm ( ) 2 $ " # 288.3nm ' # % & 6.43nm ( ) +0.16 e 2 55

Conclusions for DPA spectrum Predominant feature of the theoretical absorption spectrum of DPA consists of two closely spaced π to π* transitions, one with an electric dipole moment in the x-direction and one in the y- direction. Our SERID method qualitatively reproduces key features of the absorption spectrum, as seen experimentally and as calculated with density functional theory. Width of excitation spectrum is due to motion of the nuclei, which cause a change in the excitation energy, and additionally permit excitation to and from other molecular orbitals. 56

A final reminder of our motivation: Although real applications (such as molecular switches and biochemical detectors) will involve adaptive techniques -- with femtosecondscale laser pulses whose durations, photon energies, fluences, shapes, etc. are tailored for specific applications -- as well as larger systems, one needs an understanding of the rich interplay of electronic and nuclear dynamics to guide more empirical approaches. This understanding can be obtained through detailed studies of the kind reported here. Summary of the processes studied Cis to trans (and trans to cis) photoisomerization of azobenzene, with nuclear motion allowing extra electronic transitions for pulse durations > about 50 fs UV or visible UV or visible Photoinduced ring-opening (and ring-closing) in a model dithienylethene visible UV! Response of dipicolinic acid to femtosecond-scale laser pulses, including excited states and nuclear motion 57