1993
DOI: 10.1021/j100109a008
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The ground state of antiaromatic 1,3,5,7-tetra-tert-butyl-s-indacene

Abstract: The electronic and vibrational properties of the antiaromatic molecule 1,3,5,7-tetra-tert-butyl-s-indacene (TTBI) in the ground state are investigated in this paper. MO ab initio calculations have been performed on TTBI and the parent molecule, s-indacene (I). The results show that the C-C bonds of s-indacene alternate in length and the corresponding C2h structure is more stable than the structure without bond alternation (D2h symmetry), regardless of the basis set used. Bond length alternation is decreased … Show more

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Cited by 34 publications
(26 citation statements)
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“…Coupling these data with previous results it appears that tert-butyl substituents play a minor role in determining the ring structure, limited to the increase of the 1-8a bond [212]. Due to the hindered rotation of these groups around the C ring − C but bond several conformers occur some of which are responsible of the near-infrared S 0 → S 1 absorption spectrum when this molecule is dissolved in solution [212,213]. Table 11.…”
Section: [12]annulenesupporting
confidence: 72%
“…Coupling these data with previous results it appears that tert-butyl substituents play a minor role in determining the ring structure, limited to the increase of the 1-8a bond [212]. Due to the hindered rotation of these groups around the C ring − C but bond several conformers occur some of which are responsible of the near-infrared S 0 → S 1 absorption spectrum when this molecule is dissolved in solution [212,213]. Table 11.…”
Section: [12]annulenesupporting
confidence: 72%
“…Experimental details about the spectroscopic measurements of 'ITBI have been already reported. 6,8 TTBI solutions in a 7:3 isopentane-ether mixture were kept under vacuum in 1 mm quartz cells and quickly transferred in a low-temperature cryostat. Because of these precautions, the TTBI degradation due to air and thermal sensitivity15 was eliminated, and no signal decrease noticed during the experiments.…”
Section: Methodsmentioning
confidence: 99%
“…More recently, our group has undertaken extensive studies on a stable indacene derivative, 1,3,5,7-tetra-tertbutylindacene, and novel spectral features have been observed. [19][20][21] First, the molecule fluoresces from the second excited state,20s22 at variance with the emission behavior of most aromatics" (except a z~l e n e~~-~~) .…”
Section: Introductionmentioning
confidence: 99%