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제107회 대한화학회 학술발표회, 총회 및 기기전시회 안내 Aromatic/Antiaromatic Expanded Porphyrinoids Displaying Unique Physicochemical Property

등록일
2011년 2월 9일 10시 30분 28초
접수번호
0098
발표코드
Ⅱ-ORGN.P-216 이곳을 클릭하시면 발표코드에 대한 설명을 보실 수 있습니다.
발표시간
목 <발표Ⅱ>
발표형식
포스터
발표분야
유기화학
저자 및
공동저자
이창희, 김수진
강원대학교 화학과, Korea
New pi-extended, expanded porphyrinoid macrocycles such as naphthorosarin, naphthorubyrin, naphthosapphyrin and naphtha-octaphyrin were synthesized and fully characterized by spectroscopic means including single crystal X-ray diffraction analysis. The 24-pi naphthorosarin exhibited antiaromatic character in spite of its perfect planar structure and global conjugation of double bonds. The most prominent feature in proton NMR spectrum is that the chemical shifts of the core N-Hs appeared at 26.2 ppm, which is unambiguous indication of anti-aromatic character. On the other hand, the two-electron reduced naphthorasarin exhibited typical 26-pi aromatic characteristics. 24 pi-Naphthorosarin became exceptionally stable paramagnetic upon multiple protonation. Naphthorubyrin and naphthosapphyrin, on the other hand, displayed typical aromatic characteristics. These compounds were more basic than other expanded porphyrins. Larger hypsochromic shift of Q-bands upon protonation was observed.

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