Supporting Information

Creation of Persistent Charge-Transfer Interactions in TCNQ Polyester

Yusuke Washino,1Kimie Murata,2Minoru Ashizawa,1Susumu Kawauchi,1and Tsuyoshi Michinobu2,3,*

1Department of Organic and Polymeric Materials, Tokyo Institute of Technology, 2-12-1 Ookayama, Meguro-ku, Tokyo 152-8552, Japan.

2Global Edge Institute, Tokyo Institute of Technology, 2-12-1 Ookayama, Meguro-ku, Tokyo 152-8550, Japan.

3PRESTO, Japan Science and Technology Agency (JST).

Computational chemistry

To calculate the heat of formation, B97XD/6-31G* method was employed.1

[(4E)-4-{3,3-Dicyano-1,2-bis[4-(dimethylamino)phenyl]prop-2-en-1-ylidene}-2,5-dimethoxycyclohexa-2,5-dien-1-ylidene]propanedinitrile

Total Electronic Energy = -1714.49955204 a.u.

Optimized Structure

C / -0.38303 / -0.95695 / 2.699694
C / -0.64527 / -0.7515 / 1.372425
C / -1.51788 / -1.58087 / 0.545445
C / -0.0111 / 0.436827 / 0.715975
C / -0.97691 / 1.499416 / 0.389277
C / 1.319346 / 0.392361 / 0.398936
C / 2.112684 / 1.555019 / -0.02344
C / 3.392492 / 1.409511 / -0.45908
C / 4.055265 / 0.135895 / -0.50881
C / 3.321057 / -1.00481 / 0.039135
C / 2.048106 / -0.86393 / 0.469794
C / 5.326377 / 0.028277 / -1.03646
C / -1.26105 / -1.68894 / -0.83201
C / -2.03559 / -2.4762 / -1.65814
C / -3.14558 / -3.18875 / -1.14838
C / -3.42849 / -3.04913 / 0.22974
C / -2.63246 / -2.27267 / 1.046696
C / -1.03012 / 2.071761 / -0.88773
C / -1.97952 / 3.017584 / -1.22141
C / -2.93461 / 3.452323 / -0.2751
C / -2.89544 / 2.859148 / 1.003869
C / -1.9474 / 1.899712 / 1.313807
O / 4.015796 / -2.15212 / 0.045487
O / 1.509296 / 2.737625 / 0.116531
C / 2.219096 / 3.917667 / -0.20884
C / 3.408387 / -3.31322 / 0.571495
C / 6.110137 / -1.16319 / -1.14412
N / 6.823792 / -2.06682 / -1.28819
C / -0.84426 / -2.09151 / 3.44412
N / -1.18955 / -3.0076 / 4.066299
N / -3.92053 / -3.97352 / -1.95808
C / -5.04832 / -4.69647 / -1.40502
C / -3.62319 / -4.07297 / -3.37267
C / 5.963715 / 1.198082 / -1.55901
N / 6.44944 / 2.166739 / -1.97629
C / 0.428516 / -0.03668 / 3.444958
N / 1.068838 / 0.700125 / 4.070935
N / -3.86901 / 4.409907 / -0.59201
C / -4.89704 / 4.757019 / 0.365912
C / -3.93567 / 4.935066 / -1.93861
H / 3.964842 / 2.276064 / -0.76291
H / 1.512016 / -1.73108 / 0.831468
H / -0.41759 / -1.15712 / -1.26188
H / -1.77757 / -2.53592 / -2.70816
H / -4.28448 / -3.54594 / 0.668833
H / -2.90756 / -2.18305 / 2.091066
H / -0.31858 / 1.752301 / -1.64363
H / -1.98422 / 3.413471 / -2.22974
H / -3.61003 / 3.144666 / 1.765978
H / -1.94998 / 1.471381 / 2.312142
H / 2.511174 / 3.924281 / -1.26533
H / 1.526516 / 4.735447 / -0.01298
H / 3.10993 / 4.025032 / 0.419977
H / 3.130401 / -3.16887 / 1.62254
H / 4.159271 / -4.09825 / 0.491562
H / 2.519368 / -3.59009 / -0.00895
H / -5.80568 / -4.01621 / -0.99363
H / -4.73388 / -5.385 / -0.61066
H / -5.51836 / -5.28604 / -2.19262
H / -2.62256 / -4.48904 / -3.54752
H / -4.34845 / -4.73476 / -3.84682
H / -3.683 / -3.0956 / -3.86903
H / -5.54226 / 5.525773 / -0.06116
H / -5.52429 / 3.893905 / 0.630215
H / -4.46337 / 5.161483 / 1.289118
H / -2.99303 / 5.417338 / -2.22645
H / -4.72208 / 5.688937 / -1.99244
H / -4.16175 / 4.153832 / -2.67852

[(4Z)-4-{3,3-Dicyano-1,2-bis[4-(dimethylamino)phenyl]prop-2-en-1-ylidene}-2,5-dimethoxycyclohexa-2,5-dien-1-ylidene]propanedinitrile

Total Electronic Energy= -1714.50389247 a.u.

Optimized Structure

C / -0.70751 / -1.07729 / 2.590266
C / -0.88658 / -0.79681 / 1.264144
C / -1.98103 / -1.29619 / 0.433683
C / 0.045723 / 0.188678 / 0.63387
C / -0.57097 / 1.51008 / 0.4061
C / 1.338919 / -0.09841 / 0.291047
C / 2.277801 / 0.959248 / -0.03471
C / 3.563833 / 0.721715 / -0.37484
C / 4.074826 / -0.64518 / -0.4786
C / 3.1626 / -1.70103 / -0.13447
C / 1.877674 / -1.4623 / 0.234603
C / 5.361007 / -0.93779 / -0.88546
C / -1.78334 / -1.44588 / -0.9481
C / -2.77689 / -1.91954 / -1.7795
C / -4.05232 / -2.25166 / -1.2676
C / -4.26381 / -2.06568 / 0.116713
C / -3.2531 / -1.60574 / 0.937741
C / -0.43117 / 2.177534 / -0.81863
C / -1.03347 / 3.399392 / -1.05697
C / -1.81591 / 4.027858 / -0.06371
C / -1.97645 / 3.34438 / 1.161461
C / -1.37805 / 2.117035 / 1.377303
O / 0.989903 / -2.42719 / 0.500455
O / 4.483376 / 1.667799 / -0.62094
C / 4.103497 / 3.024042 / -0.53377
C / 1.407287 / -3.78126 / 0.494447
C / -3.2645 / 5.827869 / 0.727816
C / -1.47911 / -2.04236 / 3.314279
N / -2.07842 / -2.82932 / 3.92049
N / -2.40266 / 5.250024 / -0.28199
C / 0.349458 / -0.45957 / 3.337914
C / -2.26741 / 5.896714 / -1.56963
N / 1.189019 / 0.044688 / 3.959497
C / 6.362477 / -0.00134 / -1.29266
N / 7.239941 / 0.668101 / -1.65118
C / 5.77819 / -2.30524 / -0.94797
N / 6.081403 / -3.4252 / -0.99287
N / -5.04591 / -2.72554 / -2.08263
C / -6.34051 / -3.06218 / -1.52641
C / -4.80968 / -2.87396 / -3.50381
H / 1.930339 / 1.975964 / 0.083695
H / 3.5302 / -2.71662 / -0.20159
H / -0.81537 / -1.20479 / -1.37634
H / -2.56052 / -2.0316 / -2.83475
H / -5.23038 / -2.27418 / 0.558159
H / -3.47574 / -1.46104 / 1.988552
H / 0.146586 / 1.713908 / -1.6133
H / -0.90438 / 3.858253 / -2.02967
H / -2.57405 / 3.774041 / 1.955979
H / -1.52547 / 1.629642 / 2.336476
H / 3.778701 / 3.276413 / 0.482962
H / 3.29811 / 3.25368 / -1.24278
H / 4.99525 / 3.594954 / -0.7899
H / 2.208619 / -3.94507 / 1.222641
H / 1.746056 / -4.08136 / -0.50351
H / 0.526639 / -4.35742 / 0.776115
H / -2.72256 / 6.003266 / 1.665791
H / -4.13046 / 5.187307 / 0.94495
H / -3.63704 / 6.790122 / 0.3748
H / -2.77817 / 6.859956 / -1.54412
H / -2.70826 / 5.299676 / -2.38039
H / -1.21426 / 6.084323 / -1.81467
H / -6.83727 / -2.18562 / -1.08945
H / -6.25634 / -3.83352 / -0.75042
H / -6.98155 / -3.45209 / -2.31768
H / -4.55836 / -1.91509 / -3.97608
H / -3.99621 / -3.58255 / -3.70743
H / -5.71294 / -3.25576 / -3.98062

References

  1. Frisch, M. J., Trucks, G. W., Schlegel,H. B., Scuseria, G. E., Robb,M. A., Cheeseman,J. R., Scalmani,G., Barone,V., Mennucci,B.,Petersson,G. A., Nakatsuji,H., Caricato,M., Li,X., Hratchian,H. P.,Izmaylov,A. F., Bloino,J., Zheng,G., Sonnenberg,J. L., Hada,M.,Ehara,M., Toyota,K., Fukuda,R., Hasegawa,J., Ishida,M., Nakajima,T.,Honda,Y., Kitao,O., Nakai,H., Vreven,T., Montgomery,J. A., Peralta,Jr.,J. E., Ogliaro,F., Bearpark,M., Heyd,J. J., Brothers,E.,Kudin,K. N., Staroverov, V. N., Keith,T., Kobayashi,R., Normand,J.,Raghavachari,K., Rendell,A., Burant,J. C., Iyengar,S. S., Tomasi,J.,Cossi,M., Rega,N., Millam,J. M., Klene,M., Knox,J. E., Cross,J. B., Bakken,V., Adamo,C., Jaramillo,J., Gomperts,R., Stratmann,R. E.,Yazyev,O., Austin,A. J., Cammi,R., Pomelli,C., Ochterski,J. W.,Martin,R. L., Morokuma,K., Zakrzewski,V. G., Voth,G. A.,Salvador,P., Dannenberg,J. J., Dapprich,S., Daniels,A. D.,Farkas,O., Foresman,J. B., Ortiz,J. V., Cioslowski,J. Fox,D. J. Gaussian09 Rev.B0.1, Gaussian, Inc., Wallingford CT(2010).

1