Subject: Re: Dyes

From: Artem Masunov <[email-masked]>
Date: Tue, 23 Jan 1996 21:51:43 -0500 (EST)

[email-masked]
http://pacificnet.net/~grechtst

Dear Gregory,
	At present we are doing semiempirical (AM1) calculations on dyes.
I have output for carbocianines handly. I assume you are familiar with
MOPAC format (if not, E-mail me for datails). The first atom in the list
is the central carbon of the chain followed by pairs of symmetrical ones
with respect to it. You can calc. mean lengths from this. 
Oxacarbocianines are not ready yet. Carbocianines in different perp- and
cis-conformations and in the the first singlet excited state are also
available. Electron transition energies are within 20% with experiment.
	
Hope it helps,
Artem
      __   _________ 
     /  \ /  _   _  \   Artem Masunov - [email-masked]
    /    \\  \\  \\  \       Chemistry Department, Hunter College
   /  /\  \\  \\  \\  \          City University of New York
  /  ____  \\  \\  \\  \     695 Park Avenue, New York, NY 10021
 /__/\__/\__\\__\\__\\__\ Tel: (212) 725-0317, Fax: (212) 772-5332
 \__\/  \/__//__//__//__/
I know you believe you understand what you think I said, but I am not sure
you realize that what you heard is not what I meant. (Gaussian92)

                     SUMMARY OF   AM1   CALCULATION
                                                       Sat Nov 11 21:57:05 1995
                          AMPAC Version 5.0
                             Presented by:
  
                        Semichem, Inc.
                        7128 Summit
                        Shawnee KS 66216
                        (913) 268-3271
                        (913) 268-3445 (fax)
  
 C 27H 27N 2 
1,1'-diethiltricarbocianine
 all-Trans

     TEST ON RESIDUES SATISFIED IN BFGS OR DFP                
     SCF FIELD WAS ACHIEVED                                   

          HEAT OF FORMATION       =     270.964807 KCAL
          ELECTRONIC ENERGY       =  -33849.785723 EV
          CORE-CORE REPULSION     =   29616.109305 EV
          GRADIENT NORM           =        .467800
          DIPOLE                  =        .657291 DEBYE
          NO. OF FILLED LEVELS    =      72
          CHARGE ON SYSTEM        =       1
          IONISATION POTENTIAL    =       9.942785 EV
          MOLECULAR POINT GROUP   = CS     .100000
          MOLECULAR WEIGHT        =     379.524
          COMPUTATION TIME        =     157.58 SECONDS

          FINAL GEOMETRY OBTAINED                                 CHARGE
 AM1 SCFCRT=0.000001 CHARGE=+1 GNORM=0.01 PREC T=9999 NOXYZ +
 NOINTER
 1,1'-diethiltricarbocianine
 all-Trans
  C      .000000  0     .000000  0     .000000  0    0   0   0    -.3107
  H     1.102340  1     .000000  0     .000000  0    1   0   0     .1428
  C     1.393027  1  118.817141  1     .000000  0    1   2   0     .0839
  C     1.392972  1  118.812427  1  179.724213  1    1   2   3     .0839
  C     1.388470  1  122.660371  1  179.061606  1    3   1   4    -.3464
  C     1.388547  1  122.652878  1 -179.106235  1    4   1   3    -.3464
  C     1.414076  1  124.663173  1  177.087572  1    5   3   1     .2123
  C     1.413990  1  124.671869  1 -177.043019  1    6   4   1     .2123
  N     1.381941  1  121.200552  1  167.267610  1    7   5   3    -.1342
  N     1.381990  1  121.200214  1 -167.388434  1    8   6   4    -.1344
  C     1.460462  1  120.128545  1   -9.488228  1    9   7   5    -.0516
  C     1.460438  1  120.130507  1    9.525862  1   10   8   6    -.0515
  C     1.518778  1  114.909802  1   92.426150  1   11   9   7    -.2395
  C     1.518775  1  114.916902  1  -92.406828  1   12  10   8    -.2395
  H     1.106621  1  117.506449  1 -178.810944  1    3   1   5     .1169
  H     1.106615  1  117.505616  1  178.832629  1    4   1   6     .1169
  H     1.104245  1  116.484558  1 -178.943216  1    5   3   7     .1503
  H     1.104250  1  116.474110  1  178.924135  1    6   4   8     .1502
  H     1.129560  1  108.151838  1 -122.750398  1   11   9  13     .1204
  H     1.129038  1  107.994369  1 -122.773907  1   12  10  14     .1169
  H     1.129042  1  107.989639  1  122.773098  1   11   9  13     .1169
  H     1.129561  1  108.151901  1  122.748198  1   12  10  14     .1204
  H     1.117670  1  108.319160  1  179.776731  1   13  11   9     .1051
  H     1.117668  1  108.320245  1 -179.778728  1   14  12  10     .1051
  H     1.116701  1  111.407081  1  119.429534  1   13  11  23     .0957
  H     1.116837  1  111.379256  1  119.401825  1   14  12  24     .0956
  H     1.116835  1  111.380038  1 -119.404007  1   13  11  23     .0956
  H     1.116697  1  111.408175  1 -119.429695  1   14  12  24     .0956
  C     1.447937  1  120.385785  1  179.240789  1    7   5   9    -.2045
  C     1.447970  1  120.390749  1 -179.239257  1    8   6  10    -.2045
  C     1.358778  1  121.475063  1 -176.286217  1   29   7   5    -.0120
  C     1.358760  1  121.473554  1  176.246972  1   30   8   6    -.0121
  C     1.431380  1  120.039264  1    1.645074  1   31  29   7    -.1040
  C     1.431393  1  120.042529  1   -1.654203  1   32  30   8    -.1041
  C     1.424233  1  118.807447  1   -1.600267  1   33  31  29     .0737
  C     1.424230  1  118.805822  1    1.636628  1   34  32  30     .0737
  C     1.422528  1  118.225465  1  179.931185  1   35  33   9    -.1647
  C     1.422522  1  118.225839  1  180.060931  1   36  34  10    -.1647
  C     1.381822  1  120.328268  1    1.880293  1   37  35  33    -.0664
  C     1.381830  1  120.329320  1   -4.876080  1   38  36  32    -.0664
  C     1.405384  1  121.116119  1    -.457738  1   39  37  35    -.1320
  C     1.405372  1  121.115111  1     .431101  1   40  38  36    -.1321
  C     1.410672  1  119.981976  1 -178.973932  1   33  35  31    -.0738
  C     1.410655  1  119.981309  1  178.977665  1   34  36  32    -.0738
  H     1.101368  1  120.933020  1 -178.874895  1   37  35  39     .1522
  H     1.101367  1  120.933138  1  178.856339  1   38  36  40     .1521
  H     1.102789  1  119.526374  1 -179.674788  1   39  37  41     .1559
  H     1.102787  1  119.525449  1  179.685962  1   40  38  42     .1559
  H     1.101188  1  119.728492  1 -179.578593  1   41  39  43     .1584
  H     1.101184  1  119.729502  1  179.578176  1   42  40  44     .1583
  H     1.102098  1  120.618207  1 -179.767616  1   43  41  33     .1527
  H     1.102095  1  120.618258  1  179.765155  1   44  42  34     .1526
  H     1.103120  1  121.395352  1  178.858396  1   31  29  33     .1611
  H     1.103114  1  121.397337  1 -178.853486  1   32  30  34     .1611
  H     1.099630  1  117.805382  1  178.896448  1   29   7  31     .1626
  H     1.099623  1  117.805467  1 -178.909951  1   30   8  32     .1625
  0      .000000  0     .000000  0     .000000  0    0   0   0

                     SUMMARY OF   AM1   CALCULATION
                                                       Mon Nov 13 22:30:21 1995
                          AMPAC Version 5.0
                             Presented by:
  
                        Semichem, Inc.
                        7128 Summit
                        Shawnee KS 66216
                        (913) 268-3271
                        (913) 268-3445 (fax)
  
 C 25H 25N 2 

1,1'-diethildicarbocianine
  all-Trans

     TEST ON RESIDUES SATISFIED IN BFGS OR DFP                
     SCF FIELD WAS ACHIEVED                                   

          HEAT OF FORMATION       =     256.535841 KCAL
          ELECTRONIC ENERGY       =  -31536.844245 EV
          CORE-CORE REPULSION     =   27586.305899 EV
          GRADIENT NORM           =        .211094
          DIPOLE                  =        .065455 DEBYE
          NO. OF FILLED LEVELS    =      67
          CHARGE ON SYSTEM        =       1
          IONISATION POTENTIAL    =      10.450092 EV
          MOLECULAR POINT GROUP   = C2     .100000
          MOLECULAR WEIGHT        =     353.486
          COMPUTATION TIME        =     809.34 SECONDS

          FINAL GEOMETRY OBTAINED                                 CHARGE
 AM1 SCFCRT=0.000001 CHARGE=+1 GNORM=0.01 PREC T=9999 +
 NOXYZ NOINTER
1,1'-diethildicarbocianine
  all-Trans
  C      .000000  0     .000000  0     .000000  0    0   0   0     .0979
  Xx    1.000000  0     .000000  0     .000000  0    1   0   0
  Xx    1.000000  0  120.000000  0     .000000  0    1   2   0
  Xx    1.000000  0  120.000000  0  180.000000  0    1   2   3
  C     1.389324  1  119.132899  1 -179.226863  1    1   2   3    -.3573
  C     1.389322  1  118.704054  1  179.228540  1    1   2   5    -.3573
  C     1.415696  1  124.369437  1 -174.882117  1    5   1   6     .2162
  C     1.415726  1  124.348357  1 -174.968936  1    6   1   5     .2161
  N     1.380672  1  121.187313  1 -164.660940  1    7   5   1    -.1305
  N     1.380648  1  121.191206  1 -164.557104  1    8   6   1    -.1304
  C     1.460909  1  120.124215  1    9.072309  1    9   7   5    -.0527
  C     1.460941  1  120.120737  1    8.996532  1   10   8   6    -.0527
  C     1.518679  1  114.904520  1  -92.773645  1   11   9   7    -.2394
  C     1.518678  1  114.893892  1  -92.774716  1   12  10   8    -.2394
  Xx    1.106660  0  117.522414  0  180.000000  0    3   1   5
  Xx    1.106660  0  117.521214  0  180.000000  0    4   1   6
  H     1.103736  1  116.916721  1  179.150674  1    5   1   7     .1497
  H     1.103728  1  116.927333  1  179.139942  1    6   1   8     .1497
  H     1.129088  1  107.962584  1 -122.761086  1   11   9  13     .1186
  H     1.129082  1  107.961874  1 -122.763877  1   12  10  14     .1186
  H     1.129547  1  108.140591  1  122.743531  1   11   9  13     .1209
  H     1.129549  1  108.141157  1  122.745643  1   12  10  14     .1210
  H     1.117744  1  108.311785  1 -179.821850  1   13  11   9     .1064
  H     1.117742  1  108.312605  1 -179.793347  1   14  12  10     .1064
  H     1.116862  1  111.395554  1  119.390509  1   13  11  23     .0967
  H     1.116862  1  111.394823  1  119.387300  1   14  12  24     .0967
  H     1.116636  1  111.415857  1 -119.420940  1   13  11  23     .0940
  H     1.116640  1  111.409893  1 -119.415616  1   14  12  24     .0940
  C     1.447110  1  120.297067  1 -179.152251  1    7   5   9    -.2085
  C     1.447119  1  120.287142  1 -179.191805  1    8   6  10    -.2085
  C     1.359455  1  121.432894  1  176.542259  1   29   7   5    -.0076
  C     1.359443  1  121.429577  1  176.638358  1   30   8   6    -.0075
  C     1.430791  1  120.025499  1   -1.705369  1   31  29   7    -.1040
  C     1.430792  1  120.026242  1   -1.710711  1   32  30   8    -.1040
  C     1.424407  1  118.831042  1    1.457231  1   33  31  29     .0723
  C     1.424407  1  118.832685  1    1.420061  1   34  32  30     .0722
  C     1.422548  1  118.245536  1  180.016653  1   35  33   9    -.1642
  C     1.422561  1  118.245656  1  180.012883  1   36  34  10    -.1642
  C     1.381733  1  120.317152  1   -1.883475  1   37  35  33    -.0647
  C     1.381726  1  120.317266  1   -4.949150  1   38  36  32    -.0647
  C     1.405672  1  121.118576  1     .465402  1   39  37  35    -.1301
  C     1.405685  1  121.119970  1     .466830  1   40  38  36    -.1301
  C     1.411106  1  119.963884  1  178.964427  1   33  35  31    -.0733
  C     1.411111  1  119.963087  1  178.924915  1   34  36  32    -.0733
  H     1.101413  1  120.949741  1  178.931120  1   37  35  39     .1529
  H     1.101418  1  120.944757  1  178.920818  1   38  36  40     .1529
  H     1.102936  1  119.530210  1  179.692839  1   39  37  41     .1573
  H     1.102929  1  119.531933  1  179.659989  1   40  38  42     .1573
  H     1.101351  1  119.714419  1  179.586375  1   41  39  43     .1599
  H     1.101352  1  119.713527  1  179.610392  1   42  40  44     .1599
  H     1.102196  1  120.626163  1  179.760528  1   43  41  33     .1539
  H     1.102193  1  120.625941  1  179.741145  1   44  42  34     .1539
  H     1.103307  1  121.378015  1 -178.754890  1   31  29  33     .1626
  H     1.103302  1  121.381563  1 -178.759276  1   32  30  34     .1626
  H     1.099658  1  117.831487  1 -178.599091  1   29   7  31     .1625
  H     1.099697  1  117.823014  1 -178.570163  1   30   8  32     .1625
  H     1.105748  1  118.924740  1  179.945084  1    1   5   6     .1191
  0      .000000  0     .000000  0     .000000  0    0   0   0

                     SUMMARY OF   AM1   CALCULATION
                                                       Mon Nov 13 21:32:24 1995
                          AMPAC Version 5.0
                             Presented by:
  
                        Semichem, Inc.
                        7128 Summit
                        Shawnee KS 66216
                        (913) 268-3271
                        (913) 268-3445 (fax)
  
 C 23H 23N 2 
  pinacyanol dye, (1,1'-diethilcarbocianine)
  all-Trans

     TEST ON RESIDUES SATISFIED IN BFGS OR DFP                
     SCF FIELD WAS ACHIEVED                                   

          HEAT OF FORMATION       =     247.697887 KCAL
          ELECTRONIC ENERGY       =  -29444.262291 EV
          CORE-CORE REPULSION     =   25777.104462 EV
          GRADIENT NORM           =        .781028
          DIPOLE                  =        .688784 DEBYE
          NO. OF FILLED LEVELS    =      62
          CHARGE ON SYSTEM        =       1
          IONISATION POTENTIAL    =      11.089585 EV
          MOLECULAR POINT GROUP   = C2     .100000
          MOLECULAR WEIGHT        =     327.448
          COMPUTATION TIME        =     323.14 SECONDS

          FINAL GEOMETRY OBTAINED                                 CHARGE
 AM1 SCFCRT=0.000001 CHARGE=+1 GNORM=0.01 PREC T=9999 +
 NOXYZ NOINTER
  pinacyanol dye, (1,1'-diethilcarbocianine)
  all-Trans
  C      .000000  0     .000000  0     .000000  0    0   0   0    -.4117
  Xx    1.000000  0     .000000  0     .000000  0    1   0   0
  Xx    1.000000  0  120.000000  0     .000000  0    1   2   0
  Xx    1.000000  0  120.000000  0  180.000000  0    1   2   3
  Xx    1.000000  0  120.000000  0  180.000000  0    3   1   4
  Xx    1.000000  0  120.000000  0  180.000000  0    4   1   3
  C     1.413548  1  118.630517  1 -171.603766  1    1   2   3     .2333
  C     1.413318  1  117.020580  1 -179.568741  1    1   2   7     .2332
  N     1.381055  1  121.675550  1  157.896541  1    7   1   8    -.1319
  N     1.381140  1  121.667283  1  158.072949  1    8   1   7    -.1323
  C     1.461098  1  120.599053  1    9.719354  1    9   7   5    -.0500
  C     1.461087  1  120.603219  1    9.393301  1   10   8   6    -.0499
  C     1.518316  1  114.581538  1  -86.475508  1   11   9   7    -.2376
  C     1.518319  1  114.582537  1  -86.608505  1   12  10   8    -.2376
  Xx    1.106660  0  117.522414  0  180.000000  0    3   1   5
  Xx    1.106660  0  117.521214  0  180.000000  0    4   1   6
  Xx    1.104235  0  116.520980  0  180.000000  0    5   3   7
  Xx    1.104239  0  116.520980  0  180.000000  0    6   4   8
  H     1.128904  1  108.497535  1 -122.984618  1   11   9  13     .1212
  H     1.128947  1  108.491049  1 -122.967115  1   12  10  14     .1211
  H     1.128657  1  108.473917  1  122.934474  1   11   9  13     .1097
  H     1.128637  1  108.480889  1  122.945574  1   12  10  14     .1096
  H     1.117738  1  108.387396  1  179.923462  1   13  11   9     .1071
  H     1.117739  1  108.390016  1  179.901383  1   14  12  10     .1071
  H     1.116806  1  111.279518  1  119.352149  1   13  11  23     .0989
  H     1.116796  1  111.280025  1  119.359729  1   14  12  24     .0989
  H     1.116672  1  111.174295  1 -119.442024  1   13  11  23     .0949
  H     1.116682  1  111.175310  1 -119.442899  1   14  12  24     .0948
  C     1.448492  1  103.541286  1  178.045202  1    7   5   9    -.2192
  C     1.448583  1  104.296775  1  177.613848  1    8   6  10    -.2193
  C     1.359197  1  121.545691  1  176.925092  1   29   7   5    -.0035
  C     1.359147  1  121.546550  1  177.233362  1   30   8   6    -.0035
  C     1.430430  1  119.911663  1   -1.998991  1   31  29   7    -.1064
  C     1.430500  1  119.913177  1   -1.982799  1   32  30   8    -.1065
  C     1.424360  1  118.799554  1    3.354890  1   33  31  29     .0717
  C     1.424325  1  118.799709  1    3.379622  1   34  32  30     .0718
  C     1.422450  1  118.141360  1 -178.850855  1   35  33   9    -.1638
  C     1.422414  1  118.150069  1 -178.834218  1   36  34  10    -.1639
  C     1.382055  1  120.361255  1   -2.258445  1   37  35  33    -.0625
  C     1.382073  1  120.358054  1   -5.106249  1   38  36  32    -.0625
  C     1.405495  1  121.139650  1     .437576  1   39  37  35    -.1283
  C     1.405473  1  121.135566  1     .449390  1   40  38  36    -.1284
  C     1.411113  1  120.041118  1  179.681176  1   33  35  31    -.0721
  C     1.411059  1  120.034277  1  179.689979  1   34  36  32    -.0721
  H     1.101532  1  121.078640  1  178.268984  1   37  35  39     .1535
  H     1.101546  1  121.071485  1  178.274040  1   38  36  40     .1535
  H     1.103130  1  119.504439  1  179.545973  1   39  37  41     .1593
  H     1.103122  1  119.505456  1  179.546002  1   40  38  42     .1592
  H     1.101519  1  119.741514  1  179.488531  1   41  39  43     .1619
  H     1.101510  1  119.744709  1  179.479414  1   42  40  44     .1618
  H     1.102315  1  120.631841  1  179.764577  1   43  41  33     .1553
  H     1.102307  1  120.630750  1  179.768591  1   44  42  34     .1553
  H     1.103488  1  121.398747  1  179.953166  1   31  29  33     .1652
  H     1.103486  1  121.396387  1  179.948103  1   32  30  34     .1651
  H     1.101547  1  117.254696  1  176.503523  1   29   7  31     .1709
  H     1.101525  1  117.259105  1  176.531995  1   30   8  32     .1707
  H     1.101230  1  117.814872  1  179.967120  1    1   7   8     .1577
  0      .000000  0     .000000  0     .000000  0    0   0   0